Bruce Arena's Revs had equalised twice, including Tajon Buchanan's 118th-minute leveller, to send the game to a shootout but City goalkeeper Sean Johnson was the hero, denying Adam Buksa's tame effort.
Alexander Callens powered in the decisive penalty to clinch City's maiden Conference finals appearance, ending New England's hopes of a first-ever MLS Cup after setting a single-season record for most points with 73 in 2021.
City will take on Philadelphia Union in the Eastern Conference finals on Sunday, although they will be without top scorer Valentin Castellanos who was sent off after scoring in extra-time.
The visitors went ahead in the third minute with Santiago Rodriguez capping off a fine team move by sweeping home Tayvon Gray's cross.
The Revs levelled in the ninth minute as Polish striker Buksa headed in from Carles Gil's free-kick.
New England's Thomas McNamara headed over the bar in the second half, while Maxi Moralez's cannoned a header into the post for City.
Castellanos blew a great chance late in regulation time, before putting City ahead in extra time by emphatically powering home Gudmundur Thorarinsson's cross.
The Argentinean forward was sent off minutes later for a second bookable offence with a late tackle and the Revs capitalised with Buchanan volleying in Ema Boateng's 118th minute ball.
Buksa almost decided the contest before the shootout, bursting forward but his left-foot shot was pushed over by Johnson.
In the shootout, Johnson denied Buksa again with a low left-hand save and City converted all five of their spotkicks to secure their progress.
Tesho Akindele proved the difference for Orlando, with his 60th-minute goal seeing off Montreal in the first knockout fixture in Florida on Saturday.
Following a goalless first half, Akindele pounced on a defensive error on the hour mark – converting an easy tap-in after Clement Diop was unable to deal with Rod Fanni's back pass at Walt Disney Resort.
Nani's Orlando will face either Seattle Sounders or reigning Supporters' Shield champions Los Angeles FC in the quarter-finals.
In Saturday's other last-16 clash, Philadelphia defeated New England Revolution 1-0.
Sergio Santos' 63rd-minute effort saw the Union past Bruce Arena's Revolution.
Santos ran onto a lofted pass from Union team-mate Jamiro Monteiro and finished from an acute angle to send the Union through to the next round.
Next up for Philadelphia are either Sporting Kansas City or Vancouver Whitecaps.
The Rapids looked to have secured a point when Jonathan Lewis equalised with six minutes of normal time remaining after Diego Rubio and Jack Price had been sent off in Orlando, Florida on Friday.
But Zusi's deflected shot in stoppage time ensured Sporting KC snatched all three points in a dramatic Group D clash at Walt Disney World resort.
Colorado led through Kellyn Acosta's sixth-minute opener and it was not until the 65th minute that Sporting KC restored parity courtesy of Khiry Shelton from an acute angle.
Rapids forward Rubio was ruled to have handled Zusi's cross inside the box and sent off following a VAR review seven minutes later, and Alan Pulido converted the penalty.
After Colorado's Price was shown a straight red card for dissent moments later, Lewis found the far corner of the net to make it 2-2 in the 84th minute but Zusi's long-range attempt took a wicked deflection and looped over Rapids goalkeeper William Yarbrough in the second of 12 additional minutes.
It was Sporting KC's first win after two fixtures as they improved to three points, one point adrift of Real Salt Lake and Minnesota United.
RSL and Minnesota both had the chance to reach the last 16, however, the Western Conference foes played out a 0-0 draw.
Meanwhile, DC United salvaged a 1-1 draw against New England Revolution in Group C.
Federico Higuain – the brother of Juventus forward Gonzalo – came off the bench and rescued a point with 18 minutes remaining following Adam Buksa's opener six minutes into the second half.
DC are still searching for their first win after back-to-back draws, while the Revolution are level with Toronto on four points.
Former Valencia, Aston Villa and Deportivo La Coruna forward Gil signed for the Revs in a club-record $2million transfer in January 2019.
Gil has followed in the footsteps of Sebastian Giovinco and Carlos Vela by moving stateside during the prime of his career and quickly impressing.
Indeed, Gil suggests the reputation of MLS as a retirement league - exacerbated by high-profile deals for Frank Lampard, Steven Gerrard and Andrea Pirlo - is inaccurate.
"[MLS] has surprised me positively," he told Stats Perform News. "I believe we have a different view from Europe about what this league is.
"Probably we think it has a much lower level than it actually has, looking at players who come here to end their career. This is changing a lot and we will be aware of it as the years go on.
"I am very good. It is a different format with no relegations and playing playoffs, but it is a very attractive league to play in."
Gil contributed 10 goals and 14 goals in 2019, earning the New England captaincy, a place in the MLS Best XI and the MLS Newcomer of the Year award.
"Personally, it's been great," he said. "One of the reasons I came here was due to the confidence they showed in me.
"I wanted to get back to the level I couldn't show in previous years. Being honest, I have felt very comfortable since the beginning.
"I have performed well when I have been shown confidence, and I knew I was at the time that I needed that again. That's why I took the decision."
Gil is yet to feature in the 2020 campaign, which was suspended after just two matches due to the coronavirus pandemic.
MLS is yet to confirm plans to return, although the MLS Players Association has reportedly approved a plan to resume the season in the form of a six-week tournament in Orlando.
Any opportunity to get on the pitch is welcomed by Gil, who added: "I don't mind where and when it is, but sooner is better. And especially in the safest way possible.
"If it has to be in Orlando, let it be in Orlando. And if we can restart the league as it has always been, it is even better. My opinion is to go on, safety granted, the best way possible."
Expansion side Charlotte drew a single-game attendance record of 74,479 fans, eclipsing the 73,019 mark set by Atlanta United in the 2018 MLS Cup.
Galaxy had the better of the chances with Victor Vazquez hitting the woodwork in the 18th minute, while Javier Hernandez forced a good save from Charlotte goalkeeper Kristijan Kahlina.
Alvarez made the decisive breakthrough with a spectacular left-foot shot from outside the box which nestled into the top corner to spoil the Charlotte party.
Scottish forward Lewis Morgan netted a first-half hat-trick as New York Red Bulls won 4-1 away to Toronto.
Morgan's finishes for his opening two goals were similar, set up by Patryk Klimala with curling right-foot shots in the 17th and 24th minutes.
Jesus Jimenez pulled one back for Toronto, before Klimala released Morgan on halfway and the Scot raced forward to slot home for his treble.
Carles Gil's penalty on the stroke of half-time earned 2021 Supporters' Shield winners New England Revolution a 1-0 home win over Dallas. The victory meant Revs head coach Bruce Arena became the all-time leader among MLS coaches for regular-season wins.
Francisco Calvo scored twice in the final 10 minutes as 10-man San Jose Earthquakes salvaged a 3-3 draw with Columbus Crew.
Ola Kamara netted a stoppage-time winner for DC United as they beat Cincinnati 1-0, while Chicago Fire and Orlando City drew 0-0 and Real Salt Lake won 1-0 over Seattle Sounders.
Colorado Rapids won 3-0 over Atlanta United at home and Vancouver Whitecaps held on for a goalless draw with reigning MLS Cup champions New York City.
Sporting KC got past Houston Dynamo 1-0 while 10-man Philadelphia Union edged Montreal 2-1 and Minnesota United drew 1-1 with Nashville.
David Beckham's Inter Miami were looking to keep their fading play-off hopes alive on Saturday, however, second-half goals from New York City pair Valentin Castellanos and Talles Magno dashed that dream.
Inter Miami had never taken a point against New York City in their three previous meetings, losing all three. New York City were one of two teams Inter Miami had faced more than once without claiming a point, along with DC United.
That drought continued despite Inter Miami defender Jorge Figal initially cancelling out Castellanos' 33rd-minute opener at DRV PNK Stadium, where co-owner Beckham was in attendance.
But New York City – third in the Eastern Conference – hit back via Castellanos and Magno to clinch a play-off spot thanks to results elsewhere as Inter Miami were left to pick up the pieces in Phil Neville's first season as head coach.
Cade Cowell, meanwhile, scored a memorable solo goal as the Earthquakes outlasted Real Salt Lake 4-3 in a wild showdown.
The 18-year-old collected the ball in his own half with 21 minutes remaining before barging down the right flank, cutting in between two RSL defenders and finishing past David Ochoa with the outside of his boot.
Elsewhere, Fabio netted a dramatic stoppage-time winner as New York Red Bulls edged Montreal 1-0 to move into the seventh and final play-off spot in the east.
Defending champions Columbus Crew kept their slim play-off hopes alive with a 3-1 win over DC United, Toronto and Atlanta United drew 1-1 and 10-man Dallas edged Austin 2-1.
The Argentine stepped up to convert the 83rd minute spot-kick, extending New England's lead to 12 points from second-placed New York City in the east.
Canada international Tajon Buchanan had put Revolution ahead in the 19th minute with an excellent header and they looked good value for the win until Toronto's 79th-minute equaliser.
Jonathan Osorio levelled the game with a close-range tap-in from Pozuelo's shot across goal.
But New England found a winner, with Bou sending his penalty high to the goalkeeper's right for his 12th goal of the season. The win extends Revolution's unbeaten run to seven games.
New York City kept up the pressure in second spot with a 2-0 home win over Inter Miami thanks to a double from Valentin Castellanos, including a Panenka penalty.
The victory means City are undefeated across their past six league games, winning four of them.
New York Red Bulls slumped to their fourth defeat in five MLS games, conceding a late penalty in dramatic circumstances in a 2-1 loss at Montreal.
Former Celtic midfielder Victor Wanyama netted the 90th-minute spot-kick as the third different shooter after their previous two efforts were saved but retaken due to encroachment from keeper Carlos Coronel.
The result means the Red Bulls, who had gone ahead from Pascal Klimala's 45th-minute penalty, are winless in seven league games.
Sporting KC maintained their grip on top spot in the Western Conference with a 2-0 win at in-form Dallas.
Mexico international Alan Pulido put Sporting ahead with angled shot in the 12th minute before Daniel Salloi netted his 10th goal of the season in the 63rd minute with a sharp finish.
LA Galaxy are second in the west after Kevin Cabral's first-half strike earned a 1-0 win at Minnesota United.
Colorado Rapids scored twice in the second half to win 3-1 at Houston Dynamo, while Real Salt Lake beat 10-man Austin 1-0 to move up to sixth in the west.
In the first Los Angeles derby fixture of the MLS season, former Manchester United and Real Madrid star Chicharito guided the Galaxy to a 2-1 victory on Saturday.
Chicharito, who attempted just one shot in the loss to Seattle Sounders last time out, the sixth time in 10 MLS starts he has taken fewer than two shots (60 per cent) – he attempted fewer than two shots in just 36.7 per cent of his starts in the five major European leagues – improved his league-best tally to six goals with the 11th-minute opener at Dignity Health Sports Park, where he tucked the ball past Pablo Sisniega.
LAFC restored parity 28 minutes from the end when Diego Rossi equalised following some combination play between team-mates Latif Blessing and Corey Baird.
But the Galaxy walked away with maximum points after Chicharito teed up Jonathan dos Santos for the 79th-minute winner.
The Galaxy are second in the Western Conference, level on points with leaders San Jose Earthquakes, while LAFC are four points off the pace in eighth position.
Orlando City captain Nani stayed hot with another goal in the club's 1-1 draw against New York City.
Ex-United winger and Premier League champion Nani scored another memorable goal seven minutes into the second half, finding the back of the net with a stunning effort from the edge of the penalty area.
Nani's third goal in three games had Orlando on track for maximum points until a 77th-minute penalty via Valentin Castellanos salvaged a draw for the visitors.
"I've been working so hard and been focused on my games," Nani said post-match. "I think this is a reward [for] what you do during the week, the preparation into the games."
New York top the Eastern Conference on seven points, level with New England Revolution but a point clear of Orlando, New York Red Bulls and Nashville.
The Revolution lost 2-0 against Nashville, while the Red Bulls ran out 2-0 winners over Toronto.
Elsewhere, defending champions Columbus Crew defeated DC United 3-1, last season's Supporters' Shield winners Philadelphia Union topped Chicago Fire 2-0, Vancouver Whitecaps beat Montreal Impact by the same scoreline, Dallas and Houston Dynamo drew 1-1, while Colorado Rapids edged Minnesota United 3-2.
Sacha Kljestan netted a stoppage-time penalty to clinch all three points for Galaxy, who had been in a freefall with a winless nine-game span.
Chicharito poked in at the back post for the opening goal in the 62nd minute, pouncing on Larrys Mabiala's defensive error from Victor Vazquez's ball into the box.
The Timbers equalized 10 minutes later when Sebastian Blanco's cross-cum-shot drifted over Galaxy goalkeeper Jonathan Bond and in off the post.
Blanco hit the upright from a long-range effort, before LA won a penalty when substitute Efrain Alvarez was brought down inside the box by Josecarlos Van Rankin.
Kljestan fired low to Timbers keeper Steve Clark's right for the winner which moves Galaxy up to 42 points, retaining their grip on sixth spot in the Western Conference.
Supporters Shield-leading New England Revolution conceded late as they drew 2-2 at home with Chicago Fire.
The sides traded four goals in the second half, with Wilfred Kaptoum drilling in a low opener in the 47th minute before Alvaro Medran equalized instantly with a classy volley.
Gustavo Bou netted his 13th goal of the season to restore Revolution's lead with a deft lob from Carles Gil's lofted pass in behind the defence in the 76th minute.
Bou was denied by Chicago keeper Gabriel Slonina before Brian Gutierrez danced forward for the visitors, finding Ignacio Aliseda who fired home an angled 88th minute leveller.
Western Conference leaders Seattle Sounders missed the chance to close on New England after going down 2-1 at Houston Dynamo.
Maxi Urruti scored a spectacular volley to put Houston ahead on the quarter hour, with Darwin Quintero doubling their lead with a fine solo left-foot strike in the 20th minute.
Jimmy Medranda halved the deficit with a rifled 41st minute shot after recycling an over-hit corner, although Houston came closest to a second-half goal, hitting the woodwork four times, before Seattle's Joao Paulo had a stoppage-time free-kick cannon into the crossbar.
Real Salt Lake solidified their grip on a playoffs spot with a 3-1 home victory over Colorado Rapids, who are third in the Western Conference.
Minnesota United remained ahead of RSL by two points with a 1-0 triumph at lowly Austin thanks to Franco Frangapane's 16th-minute strike.
US international Gyasi Zardes netted a double as Columbus Crew thrashed Inter Miami 4-0, condemning them to their sixth straight defeat, during which they have scored one goal and conceded 16 times.
Luiz Araujo and Marcelino Moreno both netted late in each half as 10-man Atlanta United triumphed 2-0 at Toronto.
Junior Urso netted early as Orlando City eased past struggling Cincinnati 1-0, while DC United and Nashville drew 0-0 with the visitors recorded a draw for the fourth successive game.
The defeat means the Galaxy are winless in their past eight matches and while they dropped down to sixth in the Western Conference, their form means they could find themselves only a point ahead of the post-season chasing pack.
Former Manchester United forward Javier 'Chicharito' Hernandez stung RSL goalkeeper David Ochoa's palms early, before Damir Kreilach scored his 11th goal of the season to put the hosts 1-0 on the stroke of half-time.
Ochoa denied Chicharito again in a 57th-minute fast break, before the latter equalised with 14 minutes remaining midweek.
But in the fifth of six stoppage-time minutes, Anderson Julio lashed in a wonderful volley from outside the box to claim the win for fifth-placed RSL and boost their play-off chances.
United States teenager Ricardo Pepi netted his 12th goal of the campaign as 10-man Dallas went down 3-1 to Western Conference contenders and second-placed Sporting Kansas City.
Daniel Salloi scored a double for Sporting KC, taking his season tally to 14, while Dallas had Bryan Acosta sent off.
Seattle Sounders stayed top of the Western Conference, ahead of Sporting KC, as Raul Ruidiaz scored a brace in a 3-1 win away to San Jose Earthquakes.
Ruidiaz opened the scoring in the 25th minute, before firing home from the spot three minutes prior to the break. The Peruvian has 16 MLS goals this season, behind only DC United's Ola Kamara with 17.
Dairon Asprilla scored the winner as Portland Timbers claimed a 2-1 victory at Los Angeles FC to remain fourth in the west.
Supporters' Shield leaders New England Revolution maintained their 14-point advantage atop the Eastern Conference with a 4-1 triumph away to Montreal, extending their unbeaten run to six games.
Nashville, second in the east, blew a two-goal lead to draw 2-2 with Orlando City, while DC United got past Minnesota United 3-1.
Atlanta United boosted their play-offs hopes with a 1-0 win over Inter Miami, who have lost three in a row, while Toronto beat FC Cincinnati 3-2.
New York City suffered a second straight loss, going down 2-0 to Chicago Fire, and Philadelphia Union could only manage a 1-1 draw at New York Red Bulls.
Colorado Rapids eased past Austin 3-0 and Houston Dynamo played out a goalless draw with Vancouver Whitecaps.
Gyasi Zardes inspired Columbus in extra time of a 2-0 victory over Nashville.
The United States international's cutback found Pedro Santos to score the opener for the hosts in the 99th minute.
And, just four minutes later, Zardes sealed the win with a clinical finish in a one-on-one after being played in by Luis Diaz Espinoza.
Zardes has been directly involved in seven goals (five goals and two assists) in four matches against expansion sides over the past two MLS seasons, according to Opta.
It was enough for Columbus to reach the Eastern Conference finals for the second time in four seasons, and New England await.
After finishing eighth in the Eastern Conference, the Revolution beat Thierry Henry's Montreal Impact in the play-in round and stunned Philadelphia Union in the first round.
They continued their run with a 3-1 win over Orlando City on Sunday.
Carles Gil's 17th-minute penalty opened the scoring before Gustavo Bou made it 2-0.
Junior Urso pulled a scrappy goal back for Orlando after the half-hour mark, but their hopes of victory were hurt by Mauricio Pereyra's red card for a dangerous challenge in the 60th minute.
Still, Nani had a chance to equalise for Orlando in the 74th minute, only to see his penalty saved by Matt Turner.
The penalty save was just the second by a Revolution goalkeeper from the previous 23 on-target spot-kicks they had faced dating back to March 2016, according to Opta.
Instead, Bou got on the end of Gil's pass to poke in the sealer four minutes from time, sending New England to the Eastern Conference finals for the first time since 2014.
First-half goals from Tajon Buchanan, Emmanuel Boateng and Adam Buksa helped New England open up a 3-0 half-time lead and they never looked back.
Canada international Buchanan was critical, pouncing on a rebound to fire home the opener from close range, before dribbling in the box and providing the pass for Boateng's first-time effort.
Cincinnati pulled a goal back from record signing Brenner's 54th-minute strike but Buksa added a second on the hour, from Gustavo Bou's assist, to seal a comfortable win.
Revolution have now won four straight matches and are unbeaten in eight games. New England have scored a league-leading 44 goals this year and turned it on without injured star midfielder Carles Gil.
Benji Michel scored a 51st-minute winner as Orlando City snapped their three-game winless run with a 1-0 win over Chicago Fire to move up to second in the east.
Orlando were not helped when Nani was substituted on the half hour, but found a winner when Michel drove home after Tesho Akindele's steal.
Quinn Sullivan netted an 87th-minute equalizer to keep Philadelphia Union in touch with Orlando after a 1-1 home draw with Montreal.
Djordje Mihailovic had put Montreal ahead on the stroke of half-time before Sullivan's leveler which leaves Union two points behind Orlando.
Inter Miami continued their form resurgence with a 3-1 victory over Toronto, moving them up to 11th in the east and leaving the Canadians in last.
Mexican midfielder Rodolfo Pizarro netted a double while Robbie Robinson also scored as Inter claimed their third win in four games.
Damian Moreno scored a late winner as Atlanta United claimed their fourth consecutive win, edging DC United 2-1.
Houston Dynamo snapped their four-game losing run with 2-2 draw with Dallas in their Texan showdown, while Austin climbed off the foot of the Western Conference with a 3-1 home win over Portland Timbers.
Colorado Rapids claimed a third straight win, getting past Real Salt Lake 2-1 in the Rocky Mountain Cup while Vancouver came from behind to win 2-1 over LAFC.
After numerous delays, New York Red Bulls' derby with New York City was postponed with the pitch deemed unplayable after inclement weather as Hurricane Henri approached.
Darwin Quintero's second-half brace inspired Houston in Kansas City, where nearly 2,300 fans were allowed to attend for the first home match in nearly six months at Children's Mercy Park amid the coronavirus pandemic.
The Dynamo broke the deadlock via Alberth Elis in the 17th minute before Sporting KC's Johnny Russell equalised nine minutes later.
Houston, though, went into the interval leading 2-1 courtesy of Christian Ramirez's strike on the stroke of half-time.
Niko Hansen doubled the lead within three minutes of the restart, while Gabi Kinda reduced the deficit for Sporting KC moments later.
But Quintero's two goals in the space of four minutes just past the hour mark put the game beyond doubt.
After two defeats and four draws, Houston are ninth in the Western Conference, while Sporting KC remain four points clear atop the standings.
Elsewhere, Philadelphia Union edged New York Red Bulls 1-0 thanks to Kacper Przybylko's first-half goal.
With the win, the third-placed Union moved within four points of Eastern Conference pacesetters Columbus Crew.
Thierry Henry's Montreal Impact defeated Canadian rivals Vancouver Whitecaps 2-0, Chicago Fire accounted for FC Cincinnati 3-0, while New England Revolution prevailed 2-1 against DC United.
The victory was San Jose's first since May 7, ending an 11-match winless streak, and their first win over Seattle since September 2015, halting a 14-game drought.
Cristian Espinoza's goal in first-half stoppage time, a left-footed strike from just outside the 18-yard box, made the difference for San Jose.
San Jose thought they had another in the 89th minute but Chris Wondolowski's goal was disallowed after a video review.
New England Revolution extended their lead atop the Eastern Conference with some late magic in a 3-2 win away to New York Red Bulls.
Brandon Bye netted in the 84th minute to equalise for New England and Adam Buksa's goal in stoppage time gave the Revs their fourth straight win, leaving them eight points clear of second-placed Orlando City.
Sporting Kansas City lost a chance to move past Seattle for the top spot in the Western Conference, suffering a 2-1 defeat to Dallas as Paxton Pomykal and Jesus Ferreira netted for the visitors.
Gonzalo Higuain's second-half brace sent Inter Miami past Montreal 2-1 to end a seven-game winless streak for head coach Phil Neville's side.
DC United held on to earn a point in a 0-0 draw with Cincinnati despite having Moses Nyeman sent off in the 52nd minute and Joseph Mora in the 90th to finish with nine men.
Real Salt Lake also managed a 0-0 draw with Houston even after Justen Glad's 87th-minute red card.
Andre Shinyashiki's 29th-minute goal gave Colorado a 1-0 road win over Austin.
Cristian Dajome drew and converted a penalty four minutes into second-half stoppage time to give Vancouver a 2-2 draw with Minnesota United. Dajome had opened the scoring in the 36th minute before Ethan Finlay equalised in the 45th and Robin Lod gave Minnesota the lead after 75 minutes.
Eastern Conference leaders Columbus produced a late comeback to draw with Chicago Fire, but their lead is now just three points after Philadelphia enjoyed a win.
Philadelphia left it late to overcome New England Revolution 2-1 at Subaru Park.
With the game locked at 0-0, New England were reduced to 10 men when Matt Polster was shown a second yellow card in the 56th minute.
Just 17 minutes later and Philadelphia took the lead, Anthony Fontana chipping in from close range.
But a fine equaliser from Tajon Buchanan appeared to have New England set to earn a point.
However, there was late drama as Fontana drilled in a wonderful goal from 25 yards in the 95th minute.
Columbus appeared set for their second defeat of the MLS season when they fell 2-0 behind in Chicago.
But Fatai Alashe pulled a goal back for the Crew before Gyasi Zardes' 88th-minute equaliser.
At the bottom of the conference, Inter Miami slumped to a 2-1 loss to Orlando City.
Coming off a win over Atlanta United, Inter suffered their seventh loss in 11 games this season.
Elsewhere, the New York Red Bulls recorded a 2-0 win over DC United and New York City edged Cincinnati 2-1.
Nashville enjoyed a 4-2 win over Atlanta United, Dallas beat Houston Dynamo 2-1 and the Colorado Rapids thrashed Real Salt Lake 5-0.
Galaxy, who had endured a nine-game winless skid, had beaten Portland Timbers 2-1 on the weekend before backing that up in Houston to reinforce their grip on sixth spot in the Western Conference midweek.
Greg Vanney's Galaxy went ahead in the 39th minute from veteran Sacha Kljestan's penalty, after Maynor Figueroa brought down Kevin Cabral inside the box.
Zarek Valentin's own goal on the stroke of half-time from Efrain Alvarez's cutback doubled Galaxy's advantage.
Two minutes into the second half, Javier 'Chicharito' Hernandez provided a well-weighted pass for Kevin Cabral to add a third, moving Galaxy up to 45 points and above Real Salt Lake into fifth in the west.
New England Revolution moved another step closer to clinching the Supporters' Shield with a come-from-behind 3-2 win at DC United.
Adam Buksa, Carles Gil and Gustavo Bou all scored within 18 minutes as the Revolution responded to Nigel Robertha's 51st-minute opener for DC United.
The result moved Eastern Conference pacesetters New England to 69 points from 31 games, with Western Conference leaders Seattle Sounders closest behind them on 58 points after 30 games after they lost ground following a 1-1 draw with third-placed Colorado Rapids.
Elsewhere, Nashville – second behind New England in the east – drew for the fifth straight game in a 1-1 stalemate against defending MLS champions Columbus Crew and Cristian Arango's hat-trick guided Los Angeles FC past Dallas 3-2.
Inter Miami snapped their six-game losing skid and kept alive their faint play-off aspirations with a 3-0 home victory over Toronto.
Gudmundur Thorarinsson equalised late for New York City but their winless run extended to six games after a 1-1 draw at Atlanta United, Minnesota United were 3-2 winners against Philadelphia Union, Orlando City and Montreal played out a 1-1 draw.
Chicago Fire prevailed 4-3 over struggling FC Cincinnati, Vancouver Whitecaps came from two goals down to win 3-2 away to Portland Timbers, while San Jose Earthquakes eased past lowly Austin 4-0.
The Revolution raced to a three-goal lead but were forced to hold on in the final quarter of an hour after strikes from Patryk Klimala and Andres Reyes midweek.
Carles Gil provided the assist for all three Revolution goals, taking his season tally to an MLS-high 10, stabbing through to Canadian forward Tajon Buchanan for the 26th-minute opener.
Spanish midfielder Gil laid off for DeJuan Jones' 32nd-minute strike, before pumping the ball forward for Gustavo Bou to make it 3-0 six minutes into the second half before the Red Bulls rallied.
The win moved New England five points clear in the Eastern Conference, sitting ahead of Orlando City – who have a game in hand – and Philadelphia Union who are both on 18 points.
Jamiro Monteiro scored the only goal of the game as Philadelphia kept up their good form with a 1-0 victory over Columbus Crew.
Seattle Sounders remain unbeaten after Raul Ruidiaz's 88th-minute penalty clinched a 2-1 win against Real Salt Lake, extending their club-record unbeaten start to 10 matches.
Cristian Roldan had put Seattle ahead five minutes into the second half, reacting fastest to score from a rebound inside the box.
RSL levelled with 12 minutes to go, when they won a penalty which was converted by Slovakian Albert Rusnak.
Ruidiaz had the final say netting his eighth goal of the season with a cool Panenka finish from the spot for the Western Conference-leading Sounders.
New York City continued their rollercoaster run with a 1-0 triumph over Atlanta United via Ismael Tajouri's 69th-minute winner.
Javier 'Chicharito' Hernandez got on the scoresheet before late drama as LA Galaxy won 2-1 at Vancouver Whitecaps.
Former Manchester United and Real Madrid forward Chicharito opened the scoring, sliding home in the 47th minute with Galaxy appearing destined to claim all three points before a 90th-minute equaliser from Janio Bikel.
There would be another late twist, when the Galaxy's Efrain Alvarez scored in the third minute of stoppage – his stunning strike finding the back of the net after hopeful ball into the box.
Mexico international Carlos Vela also netted along with providing an assist as Los Angeles FC won 2-0 over Dallas.
Elsewhere, Sporting Kansas City defeated Colorado Rapids 3-1, Portland Timbers and Houston Dynamo drew 2-2, Nashville outlasted Toronto 3-2 courtesy of a 92nd-minute winner, Cincinnati edged Chicago Fire 1-0, Minnesota United beat Austin 2-0, while 10-man Montreal and DC United played out a goalless stalemate.
At the helm of Montreal, Henry's Impact came from behind to beat the New England Revolution 2-1 on the opening day of the MLS season.
The Arsenal great's side had fallen behind after just 13 minutes at Stade Olympique, where Teal Bunbury volleyed in a Cristian Penilla cross.
However, Romell Quioto headed in from close range to bring Montreal level just eight minutes before half-time.
And the hosts found an 80th-minute winner as Maximiliano Urruti spectacularly lobbed stranded New England goalkeeper Matt Turner.
Hernandez made his LA Galaxy debut in a 1-1 draw away to the Houston Dynamo.
The former Manchester United and Real Madrid forward played 90 minutes as Houston came from behind, Mauro Manotas cancelling out Cristian Pavon's opener.
Atlanta United spoiled Nashville SC's first MLS game with a 2-1 victory at Nissan Stadium.
Walker Zimmerman scored Nashville's first goal to cancel out Ezequiel Barco's opener, but Emerson Hyndman's 37th-minute strike proved to be the winner in front of a crowd of 59,069.
Elsewhere, Oswaldo Alanis' brilliant 95th-minute free-kick helped the San Jose Earthquakes hold Toronto to a 2-2 draw.
The Colorado Rapids recorded a 2-1 win over DC United, Dallas beat Philadelphia Union 2-0, Orlando City and Real Salt Lake played out a 0-0 draw and Sporting Kansas City overcame the Vancouver Whitecaps 3-1.
Higuain struck the winner in the 16th minute for Inter who have claimed 13 points from their past five matches to surge up to ninth in the Eastern Conference.
Inter had endured a six-game losing span in May and June but Phil Neville's side have bounced back, losing only once in their past 10.
The former Real Madrid forward swooped on a wayward back pass from Josh Williams, taking a touch inside the box and dinking a shot over Crew keeper Eloy Room, with Vito Wormgoor unable to clear it on the line.
New England maintained their stronghold on the lead at the top of the table with a come-from-behind 2-1 win over 10-man New York City.
Santiago Rodriguez had put City ahead with an 11th-minute volley before Revolution midfielder Emmanuel Boateng drive in a low leveller 10 minutes later. Tom McNamara may have put New England ahead when he hit the post late in the half.
Alfredo Morales was sent off for a second bookable offence, an heavy tackle on McNamara, early in the second half.
New England capitalized with in-form Tajon Buchanan coming up with a 65th minute winner from Carles Gil's assist.
Nashville maintained their strong season with a 1-0 victory on the road over Montreal after Walker Zimmerman's glancing 66th-minute header, keeping them second in the Eastern Conference behind New England.
Sporting KC struck twice inside the first 10 minutes from Jose Mauri and Johnny Russell as they won 2-0 over Chicago Fire to stay in touch with Western Conference leaders Seattle Sounders.
Colorado Rapids squandered an opportunity to temporarily go top in the west after Samuel Grandsir's late equalizer for LA Galaxy in a 1-1 draw. The Rapids instead slip to third below KC.
Seattle Sounders remained first in the west with a 1-0 home win over Minnesota United thanks to Joao Paulo's 22nd-minute strike.
Teenage sensation Ricardo Pepi scored his 12th goal of the season as Dallas drew 1-1 with San Jose Earthquakes, while lowly Houston Dynamo won 3-0 over fellow Texas outfit Austin.
New York Red Bulls continue to struggle for wins, only managing a 1-1 home draw with DC United after a controversial penalty award for a Sean Nealis handball.
Cincinnati snapped their three-game losing run with a 2-0 home win over struggling Toronto, who have lost five in a row.
Phil Neville's Inter have now claimed eight points from their past four games, having been rooted to the bottom of the Eastern Conference after six defeats in a row.
Nashville had taken the lead early in the second half from Charles Sapong but Miami responded on the hour mark.
Ex-France international Blaise Matuidi played in former Real Madrid forward Higuain who calmly collected the ball and slotted home for 1-1.
Inter dramatically claimed all three points in the 95th minute when Gonzalo's brother Federico Higuain whipped in a well-weighted cross for Indiana Vassilev to head home.
The win moves Miami out of last spot in the east and up to 12th.
At the other end of the conference table, New England Revolution moved 10 points clear with a 2-1 home win over Philadelphia Union.
Matthew Polster and Gustavo Bou netted first-half goals, sandwiching Paxten Aaronson's strike to extend New England's unbeaten run to six games.
Bou's goal came after his 39th-minute penalty was saved by Union goalkeeper Andre Blake, only for the Argentine to convert the rebound.
New York Red Bulls are winless in six after going down 2-1 to lowly Chicago Fire following Serbian midfielder Luka Stojanovic's early double strike.
DC United came from behind to win 2-1 over Montreal, while San Jose Earthquakes beat LAFC 2-1 in the Western Conference.
LA Galaxy were held to a 1-1 home draw by Vancouver Whitecaps with Kevin Cabral's 32nd-minute goal cancelled out by Ranko Veselinovic's 50th-minute reply.
