The 31-year-old winger fired in Toronto's fourth goal to make it 4-2 in the 77th minute with a near-post strike from just outside the box.
Insigne, making his third MLS appearance for Toronto, showed his class to create a pocket of space for himself before opening up his body to fire past Nashville goalkeeper Joe Willis.
The goal headlined an entertaining contest which helped Toronto claim their seventh win of the season as they seek to mount a late-season charge.
Jonathan Osorio rifled Toronto in a 19th-minute lead but Hany Mukhtar's penalty squared it up in the 41st minute. Osorio restored Toronto's lead by tapping in Richie Laryea's low ball across goal, yet Nashville were level by half-time when Teal Bunbury glanced in off the post from a corner.
Filippo Bernardeschi put Toronto up again with an emphatic 54th-minute penalty before Insigne's moment with just under quarter of an hour to go. Walker Zimmerman headed in a late goal from Mukhtar's corner but Nashville could not find an equaliser as Toronto claimed their first road win in 378 days.
Bale, making his fourth appearance for his new club, netted his second MLS goal in LAFC's 4-1 victory against Real Salt Lake.
The Walsh international came on in the 64th minute with LAFC 3-1 up after Cristian Arango's double and added the fourth with a classy solo goal. Bale ran down the right flank, beating away two defenders, before tucking into the box and finding his favoured left foot for a trademark strike.
Cincinnati made a statement with a strong 3-1 home win against Eastern Conference leaders Philadelphia Union.
All three of Cincinnati's goals came in the second half, after Brenner had a first-goal strike disallowed by the VAR. Brandon Vazquez, Brenner and Alvaro Barreal netted for Cincinnati, who move up to sixth, while Paxton Aaronson scored a late consolation for Union.
Under-performing New England snapped their six-game winless run to revive their playoffs hopes with a 3-0 victory at Orlando City.
Matt Polster, Wilfrid Kaptoum and Henry Kessler got the goals, with Carles Gil grabbing his 12th assist of the season for the latter's strike.
New York City were unable to capitalise on Philadelphia's loss, going down 3-2 at Columbus Crew, for whom Lucas Zelarayan scored a brace.
Gonzalo Higuain got on the scoresheet as Inter Miami rallied from behind to twice to manage a 2-2 draw at Montreal.
Bottom club DC United held New York Red Bulls to a 0-0 draw, while Chicago Fire made it four wins in five games with a 3-2 victory at Charlotte.
In the west, Javier Hernandez netted a late double but it was not enough for LA Galaxy who went down 4-2 at Sporting KC.
Gyasi Zardes scored a hat-trick as Colorado Rapids edged Minnesota United 4-3, Austin and San Jose Earthquakes drew 3-3 and Portland Timbers and Dallas both scored late in a 1-1 draw.
The Italy international agreed to join Toronto in January, going on to finish the 2021-22 Serie A season with 11 goals in 32 appearances for Luciano Spalletti's Napoli before heading to Canada.
Insigne scored 122 goals in 434 appearances for his hometown club, a tally which is only bettered by Dries Mertens (148) and represents seven goals more than the late, great Diego Maradona netted for the Partenopei (115).
Speaking at his first news conference in Toronto, Insigne refuted the suggestion that MLS represented a step down for a player of his quality.
Asked whether he had been presented with other options, Insigne said: "I didn't receive any [other] offers at that time. It was very early when I first met the president, and I still had my contract with Napoli. I could have stayed in Europe.
"I'm 31, so I still have many years in front of me, but I wanted to choose happiness and the wellbeing of my family.
"As I mentioned before, I won a lot with Napoli, and I lost as well. But I wanted a change and more importantly, a challenge, either in another European club or here in North America.
"I've heard people saying that soccer in North America is not real soccer, but I've seen it and it's not true.
"It is a challenge because of the move, but I'm really grateful to the opportunity the president gave me and the whole organisation has given me, and the love and the effort that everybody is putting into this. I'm very thankful, and I want to repay the love with my performances during the season."
Insigne joins a team that sits 11th in the Eastern Conference, but he is already targeting silverware.
"I am very happy to be here. This is a big and new adventure for me and my family, this is the first time we have been away from Napoli," he said.
"But it was a great choice, because when I first met the president, he talked to me about Toronto as a city and especially about the team.
"He struck me as a really great person, and the project that he explained to me about the team stuck with me.
"I made the decision, not for the money, but for a new life for my family and my kids, and for their wellbeing. The project is certainly a challenge, and I would like to be part of winning the championship.
"I played for Napoli for 10 years and for the Italian national team, winning the Euros. So, I don't have any problem with being under pressure, and I'd rather have my actions speak for me on the pitch."
Federico Redondo scored twice in the second half to add to Diego Gomez's opener, with Derrick Etienne netting a late consolation for the visitors.
FC Cincinnati's 1-0 loss to Chicago Fire ensured the Herons returned to top spot, bouncing back from their 6-1 defeat to their Queen City rivals last time out.
Lionel Messi, who is recovering from an ankle injury following Argentina's Copa America success, watched on as his side almost fell behind only for Deandre Kerr to fluff his lines inside the area.
That opportunity would be capitalised on three minutes before the break, with Gomez firing the ball beyond Sean Johnson for the first real moment of magic in the contest.
Toronto continued to create chances, with Federico Bernardeschi almost providing an instant response only to see his curling effort saved brilliantly by Drake Callender.
But Inter Miami would increase their advantage shortly after the interval, with Redondo heading in at the back post following Julian Gressel's teasing delivery.
The Argentine would double his tally for the evening, and the season six minutes later, rounding off a superb team goal with a neat finish inside the area.
John Herdman's side would get themselves on the scoresheet heading into the final 10 minutes with Etienne placing the ball into the far left corner.
But Inter Miami would hold on to secure a 15th triumph of the season, ahead of their final fixture before the Leagues Cup against Chicago Fire this weekend.
The win means Phil Neville's side are unbeaten in five games and have won three of their past four to move up to fifth spot in the east.
All the goal scoring action occurred in the first half, with Inter going ahead after Toronto goalkeeper Alexander Bono's inexplicable error from Jean Mota's hopeful long-range strike in the 24th minute.
Italian recruit Lorenzo Insigne produced a moment of magic with a low right-foot volley to equalise four minutes later.
But Inter restored their lead in the 44th minute with a classy set play from a free-kick ending with Damion Lowe nodding back for Ariel Lassiter to stab home from close range.
Toronto midfielder Michael Bradley forced a save in the 72nd minute while Filippo Bernardeschi had a 94th-minute penalty shout waved away for the visitors.
Eastern Conference leaders Philadelphia Union flexed their muscle with Julian Carranza netting a hat-trick in a 6-0 away win over struggling DC United.
Philadelphia were in a ruthless mood although it was scoreless until Mikael Uhre got free and squeezed in the opener in the 37th minute.
Daniel Gazdag netted a penalty won by Uhre on half-time, before Carranza scored three goals inside 27 second-half minutes capitalizing on some inexplicable passing from the United defence. Cory Burke curled in the sixth in the 79th minute.
Reigning MLS Cup champions LAFC went down 2-1 at San Jose Earthquakes but became the first side to book their playoffs spot by virtue of other results.
Colorado Rapids drew 1-1 with Houston Dynamo, who found a late equaliser from Sebastian Ferreira, while Vancouver Whitecaps could only draw 1-1 at Real Salt Lake, locking in LAFC.
Kei Kamara moved into outright third in the MLS goal scoring charts with his 135th career league goal as Montreal defeated New England 4-0.
Matt Miazga marked his return to the MLS with a goal in his second game for FC Cincinnati as they drew 1-1 at his former club New York Red Bulls.
Minnesota United boosted their playoffs' hopes with a 2-1 win over Austin thanks to Franco Fragapane's 62nd-minute winner.
Pozuelo, crowned MLS' best player in 2020 in the second of a three-and-a-half-season stay with Toronto, will occupy an International Roster slot and a Designated Player slot for Inter.
Phil Neville's side will pay $150,000 in General Allocation Money (GAM) to Toronto across two years for the signing of Pozuelo, which is subject to the Spaniard receiving a P-1 Visa.
Toronto will also retain a sell-on percentage in the event of a future transfer, while Inter will send additional conditional GAM if Pozuelo meets certain performance-based incentives.
"We're thrilled to be able to welcome a player of Alejandro's calibre," Inter sporting director Chris Henderson said.
"He has proven himself to be one of the brightest talents in the league and we are confident that will continue here in South Florida.
"We were looking to add a decisive, creative attacking player and we feel he fits the profile."
Prior to joining Toronto, where he scored 30 goals and assisted 34 in 100 appearances across all competitions, Pozuelo played for Real Betis, Swansea City, Rayo Vallecano and Genk.
As well as winning the MVP award two years ago, the 30-year-old was also twice named in the MLS Team of the Season.
"We believe Alejandro will fit right in with our group," head coach Neville said. "He's a player of tremendous quality that we feel can be a real game changer for us.
"We can't wait to integrate him into the squad and are looking forward to seeing him on the pitch in Inter Miami colours."
Pozuelo's departure from Toronto comes amid widespread speculation that the Canadian club are closing in on a move for former Juventus midfielder Federico Bernardeschi.
The Italy international, who left the Bianconeri as a free agent when his contract expired last month, has secured a four-year deal with the MLS franchise.
Bernardeschi is the third Italian to join Toronto during this window, with Lorenzo Insigne and Domenico Criscito also arriving in Ontario.
The three-time Serie A title winner brings plenty of experience to the Reds' ranks, having also racked up 182 appearances for Juventus across all competitions, scoring 12 goals while providing 20 assists.
The 28-year-old winger has also earned 39 senior international caps and was part of Italy's Euro 2020-winning squad, scoring his spot-kick as the Azzurri beat England on penalties in the final.
"Having met with Federico a couple of weeks ago, we think he's a great fit for what we're trying to build here at TFC, and look forward to getting him on the field," said Toronto head coach and sporting director Bob Bradley.
Club president Bill Manning added: "We are thrilled to add Federico to our team. As a player and a person, we believe he's exactly what we need right now, both on the field and in the locker room.
"Federico has proven himself to be a champion and a leader at Juventus and for the Italian national team, and brings a pedigree to Toronto that's second to none."
Toronto are 13th in the Eastern Conference and aiming to end a four-game winless run when they travel to Montreal on Sunday.
Marco Delgado's strike in the sixth minute was enough to separate the two sides as the Galaxy moved to third on 19 points, a point behind Austin and four points from rivals Los Angeles FC atop the conference.
In what was a sluggish opening, Delgado intercepted the ball high up the pitch and struck home from just outside the penalty area to put the Galaxy in front, with the ball deflecting in off the post and past Andrew Tarbell in the Austin goal.
For all their possession in the second half, Austin's best chance came via a dead ball from Sebastian Driussi, who hit the post in the 89th minute.
In contrast, Galaxy were not able to capitalise from a number of opportunities in transition, but they were still able to emerge with a vital three points.
Earlier on Sunday, the Vancouver Whitecaps defeated Toronto FC 1-0 in the all-Canadian matchup, but remain bottom of the Western Conference.
After Thomas Hasal saved Alejandro Pozuelo's penalty in the 34th minute, substitutes Lucas Cavallini and Tosaint Ricketts combined for the Caps, with Ricketts scoring the winner against his former team in the 90th minute.
In Sunday's other result, Nashville SC defeated Real Salt Lake 2-0. David Romney found the breakthrough in the 63rd minute, before C.J. Sapong sealed it in stoppage time.
Akinola, 20, starred with a hat-trick in Toronto's thrilling 4-3 victory over the Montreal Impact at the Walt Disney World Resort in Florida.
The United States youth international helped Toronto to their first win in Group C, while Montreal were left without a point.
Toronto opened the scoring in the eighth minute through Richie Laryea, who cut inside from the left before finding the bottom corner.
Romell Quioto's finish in a one-on-one brought Montreal level before Akinola got on the end of an Alejandro Pozuelo cross to make it 2-1.
After a Saphir Taider penalty again levelled the contest, Akinola restored Toronto's lead following a Pozuelo pass.
Akinola showed off his strength before completing his hat-trick and Toronto held on despite another Taider penalty deep into additional time.
Columbus Crew booked their spot in the last 16 from Group E after a second straight win, beating the New York Red Bulls 2-0.
Gyasi Zardes opened the scoring before Lucas Zelarayan's low strike in the second half.
Jesus Medina, Valentin Castellanos and Maxi Moralez were on target for New York City, who defeated Toronto 3-1 in Orlando, Florida on Sunday.
Medina gave NYC, led by former Celtic boss Ronny Deila, the perfect start after just five minutes at Walt Disney Resort – firing a shot through the hands of Toronto goalkeeper Quentin Westberg.
New York City doubled their lead 10 minutes into the second half when Castellanos ran onto Moralez's no-look pass and beat Westberg with a powerful effort.
Moralez made it 3-0 with nine minutes remaining before Patrick Mullins pulled a goal back six minutes later after combining with Jozy Altidore.
Awaiting NYC in the quarter-finals are either Portland Timbers or FC Cincinnati.
Melia, meanwhile, produced some penalty heroics to lead Sporting KC past Vancouver Whitecaps 3-1 in a shoot-out.
After a goalless 90 minutes, Melia saved two spot-kicks as Gianluca Busio stepped up to convert the winning penalty.
No goalkeeper has saved more penalties – excluding shoot-outs – in MLS since the start of the 2015 season than Melia.
Sporting KC will face Philadelphia Union for a spot in the semi-finals.
The league followed the NBA in postponing games on Wednesday after the Milwaukee Bucks went on strike in protest against police brutality and racial inequality.
Blake, a black man, was repeatedly shot in the back by police in Wisconsin, the Bucks' home state.
Just one MLS match went ahead on Wednesday, with Orlando City beating Nashville, but the players are now ready to resume play. The NBA will return on Saturday.
"Following a period of reflection and conversation with the Black Players for Change (BPC), the league's players and the MLS Players Association, matches will resume, beginning tonight with the Montreal Impact hosting Toronto FC," a statement read on Friday.
"BPC are scheduled to meet with MLS owners, as the players and the league continue working together to create long-term change both inside and outside of MLS."
MLS bosses have largely supported the teams in their demonstrations, although Real Salt Lake owner Dell Loy Hansen sparked outrage as he criticised his club and threatened to cut funding.
RSL players past and present hit back, while Toronto striker Jozy Altidore and NBA playoff star Donovan Mitchell - a player for Salt Lake City's Utah Jazz - each called on Hansen to sell the team.
Salt Lake defender Nedum Onuoha told the BBC he was considering his future at the club after Hansen's comments.
"I don't want to be here, because I’m not here to play for someone who isn’t here to support us," the former Manchester City centre-back said.
"We are trying to create a bigger conversation, but a lot of the people who are in power don’t empathise or sympathise or do anything. They are more concerned with themselves."
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.
Lewis Morgan's brace helped David Beckham's Inter defeat Eastern Conference rivals Atlanta United 2-1 in Miami on Wednesday.
In the midst of a three-game winless streak and with just five points from their nine regular-season matches, expansion franchise Inter opened the scoring through Morgan midweek.
A 28th-minute counter-attack led by Rodolfo Pizarro resulted in former Celtic winger Morgan beating Atlanta goalkeeper Brad Guzan from an acute angle.
Atlanta equalised five minutes later when Eric Remedi put the ball over the line from his position on the ground after his initial backheel was blocked by Andres Reyes.
The winning goal came seven minutes before half-time – Morgan restoring Inter's lead with a curling finish from the top of the penalty area.
But not before some wild penalty drama, starting in the 40th minute. Inter goalkeeper Luis Robles saved Ezequiel Barco's attempt but Erick Torres crashed in to convert the rebound.
It was ruled out for encroachment, however, following a video review, though Barco was given a retake after Inter were also penalised for encroachment but Robles thwarted the Atlanta attacker again.
Inter are 13th in the 14-team Eastern Conference, three points adrift of eighth-placed Atlanta and 15 behind leaders Columbus Crew.
Toronto are second and two points adrift of the Crew following their last-gasp 2-1 win at Canadian rivals the Impact.
Pablo Piatti's 32nd-minute opener had been cancelled out by Montreal's former Tottenham midfielder Victor Wanyama eight minutes into the second half.
But Altidore popped up with the winner in the 89th minute, finishing under onrushing Impact goalkeeper Clement Diop, snapping Toronto's run of back-to-back defeats.
Elsewhere, Real Salt Lake accounted for slumping Supporters' Shield holders Los Angeles FC 3-0, Minnesota United edged Dallas 3-2 and Lalas Abubakar's 96th-minute equaliser salvaged a 1-1 draw for Colorado Rapids against in-form Houston Dynamo.
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.
With Tuesday's contest seemingly heading for a draw, Inter Miami's Makoun stepped up and scored a spot-kick in the 95th minute.
Unbeaten in six matches, Inter Miami – co-owned by former Manchester United, Real Madrid and England star Beckham – have won three consecutive matches for the first time in their history as they moved into the Eastern Conference play-off positions.
Toronto had just 15 points through 23 matches entering the matchup. Only five teams in MLS history have had fewer points at this stage of a season, most recently DC United in 2013 (13).
Kemar Lawrence was sent off in the 37th minute but Toronto thought they had snatched a winner with two minutes of regulation remaining when the hosts believed Jacob Shaffelburg's rebound crossed the line.
Inter Miami went up the other end and claimed all three points in the fifth minute of stoppage time – Makoun fouled by Chris Mavinga before tucking away the last-gasp penalty.
Following four consecutive clean sheets – a club first, Inter Miami are fifth in the east with 32 points from 23 rounds, while Toronto sit bottom after six straight defeats and nine games without a win.
Elsewhere, New York City and Dallas played out an entertaining 3-3 draw.
New York – fourth in the Eastern Conference – led 2-1 and 3-2 but had to settle for a point in a see-sawing contest at Red Bull Arena.
As for MLS champions Columbus Crew, they overcame New York Red Bulls 2-1 thanks to an 88th-minute goal via substitute Miguel Berry.
Columbus had lost six in a row and appeared on the verge of another defeat, trailing 2-1 at home after Isaac Atanga's 74th-minute goal gave Cincinnati the lead.
Berry had come on for Shaun Wright-Phillips a minute earlier, and he soon became the hero of the hour for the Crew.
The 23-year-old put home a rebound from a Pedro Santos shot in the 81st minute, then watched another rebound from an Alex Matan effort bounce off his chest and into the net less than two minutes later.
Columbus earned their first win since July 24 while Cincinnati saw their winless run extended to 11 (4L, 7D).
Montreal rolled to a 3-1 defeat of Toronto as the visitors were forced to play with 10 men for nearly the entire game.
Noble Okello picked up a straight red card after five minutes, condemning the visitors to a fourth straight defeat.
Samuel Piette, Joaquin Torres and Romell Quioto scored for Montreal, the latter two goals proving the difference after Ifunanyachi Achara had equalised for Toronto in the 58th minute.
Inter Miami earned a 0-0 draw at Orlando City thanks in part to Nick Marsman's first-half save of a Tesho Akindele penalty kick.
It was just the second clean sheet of the season for Phil Neville's side, while Orlando City are now unbeaten in six matches (2W, 4D).
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.
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.
