Alexander Zverev saved a match point and battled back to salvage a dramatic victory over Jenson Brooksby at the Mexican Open in what was the latest finish in tennis history.

Second seed Zverev – the defending champion in Acapulco - wrapped up a dramatic win at 04:55 local time after his own lengthy contest had followed two other epic three-setters earlier on the schedule.

Zverev at one stage looked like he was on the way out but ultimately triumphed 3-6 7-6 (12-10) 6-2 to book a second-round tie against Peter Gojowczyk.

The German had beaten Brooksby in a match that also went to a decider when they clashed at Indian Wells in October and he was pushed to the limit again in a battle lasting 200 minutes.

Having dropped the first set, Zverev had to fend off three break points at 3-3 in the second and saved a match point at 6-5 as part of an epic tie-break that went in his favour. 

Zverev was then more comfortable as he broke twice in the decider to seal victory, his American opponent paying the price for converting just one of his seven break-point opportunities in a match that made history for its late finish.

Elsewhere, Stefan Kozlov overcame cramps in the second set to outlast Bulgarian Grigor Dimitrov 7-6 (10-8) 5-7 6-3, with that match lasting three hours and 21 minutes.

John Isner sent down 29 aces and saved a match point as he trailed 5-2 in the third set, ultimately winning 7-5 6-7 (4-7) 7-6 (7-3) over veteran Fernando Verdasco in another epic topping the three-hour mark that helped to push back the start time for Zverev and Brooksby.

Seventh seed Taylor Fritz got past Frenchman Adrian Mannarino 6-3 6-3, while Dusan Lajovic knocked off Sebastian Korda 6-4 4-6 7-5 and eighth seed Pablo Carreno Busta beat Oscar Otte in straight sets.

At the Chile Open in Santiago, eighth seed Facundo Bagnis won 6-3 6-0 over Bernabe Zapata Miralles in the round of 32.

Brazilian Thiago Monteiro got past local Nicolas Jarry 7-6 (11-9) 6-4, while qualifier Juan Ignacio Londero and wildcard Thiago Seyboth Wild also progressed.

Rafael Nadal fended off a battling Emil Ruusuvuori to reach the Melbourne Summer Set final as the Spanish veteran bids to land the 89th singles title of his stellar career.

Nadal, who has won at least one ATP Tour tournament in every season from 2004 onwards, will look to extend that streak into a 19th year after scoring a 6-4 7-5 win on Rod Laver Arena.

He has not captured a title in Australia since 2009, when he landed his only Australian Open triumph to date by beating Roger Federer.

Nadal will be a strong favourite against American qualifier Maxime Cressy in Sunday's final, despite being made to work hard to see out victory over 22-year-old Ruusuvuori.

The 35-year-old Mallorcan looked set for a routine win but dropped serve at 5-3 in the second set, allowing world number 95 Ruusuvuori a path back into the contest.

It provided Nadal with a test of resolve that he came through, tying up victory in an hour and 56 minutes, an encouraging sign as he continues to battle for full sharpness after a near five-month absence.

Nadal acknowledges he may not have long left in tennis, and he wants to make the most of the opportunities that remain.

"I just love what I'm doing," he said in an on-court interview. "I always feel passionate about the sport in general and I feel a very lucky person that I can live from one of my hobbies, tennis.

"I know it's not forever and it's not a job I'm going to do for 50 years, but I want to enjoy it as much as I can while I still have the chance."

The foot injury that caused the 20-time grand slam winner to curtail his 2021 season in August has not prevented him finding winning form this week and now Paris-born Cressy awaits, with the 24-year-old world number 112 enjoying a remarkable week.

Cressy was a 7-5 7-6 (11-9) winner on Saturday against Bulgarian third seed Grigor Dimitrov, serving 17 aces on the way through to his first ATP Tour final.

At the Adelaide International 1 event, Gael Monfils will face Karen Khachanov for the trophy.

Top seed Monfils ended the spirited run of Australian wildcard Thanasi Kokkinakis, earning a 7-5 6-0 semi-final win, while second seed Khachanov battled past former US Open champion Marin Cilic 7-6 (7-3) 6-3.

Rafael Nadal declared his first singles match on the ATP Tour for five months a roaring success after the Spaniard battled past Ricardas Berankis in Melbourne.

A 6-2 7-5 win for Nadal over the Lithuanian qualifier carried the 35-year-old into the quarter-finals of the Melbourne Summer Set tournament.

Playing on Rod Laver Arena, the main show court for the upcoming Australian Open, top seed Nadal was tested by Berankis but came through unscathed, breaking serve to love to clinch the victory.

This was the first time that Nadal had faced Berankis, the world number 104 who briefly entered the top 50 five years ago, and it came as the 20-time grand slam winner battles back from the left foot injury that curtailed his 2021 season.

Nadal had not competed on tour since losing to Lloyd Harris in the third round in Washington in August, and the match practice he gained at an exhibition event in Abu Dhabi last month was followed by him contracting COVID-19.

He is vaccinated though, so was able to travel once he recovered from that brush with coronavirus, and is looking to build up form and fitness before the Australian Open begins.

"Honestly, I've been going through some difficult, challenging moments the last year and a half, but in general terms I'm super happy to be back in competition," Nadal said.

"It's important to start with a victory. It gives me the chance to play another time tomorrow and that's the main thing at this moment because I didn't play for such a long time.

"The main thing is being healthy. That's probably the only thing."

Awaiting Nadal in the last-eight stage will be Dutch player Tallon Griekspoor, who fended off Australia's Alexei Popyrin in three sets.

Determined not to take on too heavy a workload, Nadal has pulled out of the doubles tournament, despite making a winning start on Tuesday when he paired up with fellow Spaniard Jaume Munar.

He elected to play doubles initially to build up some rhythm. "In doubles, things always happen fast," Nadal said. "It makes you feel alive on the tour again. I think that was a positive thing."

Third seed Grigor Dimitrov advanced, seeing off Andy Murray's conqueror Facundo Bagnis in three sets, but Belgian fourth seed David Goffin slumped to a 7-5 6-3 loss against Slovakian Alex Molcan.

At the Adelaide International 1 tournament, there were wins at the last-16 stage for the top three seeds – Gael Monfils, Karen Khachanov and Marin Cilic – but fourth seed Frances Tiafoe was caught out by Australian Thanasi Kokkinakis, losing in three sets.

Defending champion Daniil Medvedev set up a showdown with Novak Djokovic in the Paris Masters final after dismissing Alexander Zverev in straight sets.

The Russian, who downed Djokovic in the final of this year's US Open, was at his imperious best to see off Zverev 6-2 6-2 in the French capital.

He will now attempt to deny Djokovic a sixth title at the ATP 1000 event on Sunday, while seeking to etch his own name onto the trophy for a second year running.

World number two Medvedev, who overcame Zverev in the final of this event in 2020, ended the German's run of eight consecutive victories in style.

It took just 80 minutes for Medvedev to get the job done, his flat groundstrokes posing questions that Zverev had no answers to.

While Zverev did apply some pressure by forcing his rival to face three break points, Medvedev was cool under pressure as he held serve throughout the contest.

This triumph drew Medvedev level at 5-5 in the pair's head-to-head record.

He will likely face a sterner test against Djokovic, whose come-from-behind win over Hubert Hurkacz ensured he will claim the year-end number one ranking for a record seventh time.

On Sunday, he will bid to set another record by moving ahead of Rafael Nadal to reach 37 titles in Masters 1000 tournaments.

Alexander Zverev was given a thorough examination of his Paris Masters credentials by Grigor Dimitrov, but the fourth seed progressed nonetheless to reach the last eight.

Zverev, who last in last year's final, saw match points slip from his grasp in the second set as Dimitrov levelled the match, however, he eventually prevailed on Thursday.

World number one Novak Djokovic benefited from a walkover, while Daniil Medvedev also moved through to the quarter-finals of the ATP Masters 1000 event.

Zverev outlasts Dimitrov

Olympic Games gold medallist Zverev had to dig deep for his 7-6 (7-4) 6-7 (3-7) 6-3 win over former world number three Dimitrov.

It was Zverev's seventh win on the bounce, but he was well aware of just how deep he had to dig to see off a resilient Dimitrov.

"Incredible match," Zverev, who won a fifth tour title of the year last week at the Vienna Open, said afterwards. "Grigor is playing very high-level tennis and I had to leave everything out there.

"I think it was a very high-level match and it could have gone both ways, especially the third set. I am happy with how things went in the end."

Djokovic moves through without playing

There was no such ordeal for top seed Djokovic, however.

Djokovic – a 20-time grand slam champion – received a walkover after Gael Monfils was advised not to continue with the tournament due to an adductor issue sustained in his previous win over Adrian Mannarino.

Taylor Fritz awaits five-time Paris champion Djokovic after the American saw off 10th seed Norrie 6-3 7-6 (7-3), while Casper Ruud will tussle with Zverev.

Ruud's emphatic 6-2 6-1 demolition of Marcos Giron clinched a historic achievement for the 22-year-old – who became the first Norwegian to qualify for the ATP Finals at the end of a breakthrough year in which no player can better his five tour-level titles.

Hubert Hurkacz did his chances of joining Ruud in Turin no harm as the Polish seventh seed – who holds the last automatic qualifying berth – fought back to defeat Dominik Koepfer 4-6 7-5 6-2 and set up a meeting with James Duckworth, who beat Alexei Popyrin 7-6 (8-6) 6-4.

Second seed and US Open champion Medvedev was another who had to come from behind before ultimately seeing off Sebastian Korda 4-6 6-1 6-3.

He will go up against Hugo Gaston, who became the first French qualifier to reach the Paris Masters quarter-finals since 1990 with his win over Carlos Alcaraz.

ameron Norrie continued his sensational year by reaching his sixth and most significant final for the season with a straight-sets win over Grigor Dimitrov in the Indian Wells Masters semi-finals on Saturday.

The British 21st seed claimed his 46th win for the season, earning his sixth final appearance for the season, which is the equal most of any male player on tour, alongside Novak Djokovic.

Norrie will play Georgian 29th seed Nicoloz Basilashvili who defeated local Taylor Fritz in straight sets to reach a Masters 1000 final for the first time.

NORRIE TOPPLES TIRING DIMITROV

Norrie will also be making his maiden Masters 1000 final appearance after a 6-2 6-4 victory over 23rd seed Dimitrov in one hour and 26 minutes.

The 26-year-old Briton got ahead in both sets with an early break to set up the victory. Norrie moves ahead of Daniil Medvedev, Casper Ruud and Stefanos Tsitsipas and level with Djokovic for most final appearances this season.

"I've been playing a lot of big matches this year, which has helped," Norrie said during his on-court interview. "I feel like I am used to the big moments and the big matches.

"I'm feeling more and more comfortable and I feel like I am playing on my terms in key moments."

Dimitrov, who beat top seed Daniil Medvedev in an epic fourth round comeback, appeared spent physically with 31 unforced errors compared to Norrie's 19, with the Briton only hitting 12 winners for the match.

The triumph boosts Norrie's hopes of qualifying for the ATP Finals, with victory in the decider to see him move past Jannik Sinner into 10th position and within 125 points of the last position, currently occupied by Hubert Hurkacz.

BASILASHVILI MAKES MAIDEN MASTERS 1000 FINAL

Basilashvili overcame late nerves to secure his first-ever Masters 1000 final berth with victory over 31st seed Fritz in 7-6 (7-5) 6-3 in one hour and 41 minutes.

The 29-year-old, who had never won a main draw match at Indian Wells prior to this year's event, had 26-21 winners for the match, stepping up in the key moments to claim his breakthrough spot in a decider.

"It means a lot, especially at Indian Wells," Basilashvili said during his on-court interview. "People call this the fifth grand slam so it means a lot."

The Georgian was uncompromising and committed throughout, staving off three Fritz set points in the first set, before getting the lead in a tiebreak. Basilashvili converted his first break point for the match to lead 4-2 in the second set, although he spurned three match points with missed forehands, before sealing victory.

"For me, I'm first time experiencing semi-finals, finals and quarter-finals so I'm really tight," Basilashvili said. "It's natural but I try to get rid of it as much as I can. If I focus on my game and play, I can play good tennis."

Grigor Dimitrov continued his red-hot form with a hard-fought victory over Hubert Hurkacz at the Indian Wells Masters, where Cameron Norrie awaits in the semi-finals.

After conquering top seed Daniil Medvedev, former world number three Dimitrov recovered from a set down to upstage eighth seed Hurkacz on Thursday.

Norrie shocked 11th seed Diego Schwartzman in straight sets at the ATP 1000 tournament.

DIMITROV CELEBRATES MILESTONE

Bulgarian star and 23rd seed Dimitrov reached his first ATP Masters 1000 semi-final of the season with a 3-6 6-4 7-6 (7-2).

Dimitrov showed he is the comeback king once again, having also saved two break points at 3-3 in the second set.

A semi-finalist at the US Open (2019), Australian Open (2017) and Wimbledon (2014), Dimitrov then squandered a 5-2 lead in the deciding set before eventually prevailing in a tie-break for his 100th Masters 1000 victory.

NORRIE BOOSTS TURIN BID

Norrie's hopes of qualifying for the ATP Finals in Turin received a boost after breezing past Schwartzman 6-0 6-2.

Amid a career-best season, Norrie advanced to his maiden ATP Masters 1000 semi-final, with the 26-year-old to replace Daniel Evans as the new British men's number one.

Seeded 21st, Norrie – who has 45 Tour-level wins in 2021 – now has next month's Finals firmly in sight, having started the day 945 points behind ninth-placed Hurkacz in the race to Turin.

"I have been pretty consistent this year," Norrie said after 74 minutes on court. "I think I am really doing the fundamentals well on serve and return and playing the big points better.

"I have been a little more aggressive and feel I am learning more as I go along and becoming more experienced. We are really happy."

Daniil Medvedev was ousted from the Indian Wells Masters, the US Open champion and top seed stunned by former world number three Grigor Dimitrov in a thrilling comeback.

Dimitrov had been a set and a double break down against the Russian star on Wednesday, before launching a remarkable rally for his first win over a top-two opponent since 2016.

Meanwhile, second seed Stefanos Tsitsipas and third seed Alexander Zverev both won to secure their spots in the last eight.

MEDVEDEV SHOCKED IN THE DESERT

Dimitrov roared back to triumph 4-6 6-4 6-3 over Medvedev, who had won 18 of his past 19 matches on North American soil.

Bulgarian star Dimitrov trailed 4-1 in the second set after dropping the opener before stunning the first-time grand slam champion midweek.

"I just felt something at 1-4 and I calmed myself down and started to take better decisions and started to control the pace of the game, which I really believed helped me," Dimitrov – the 23rd seed – said. "In the end it was just very solid and smart play."

Dimitrov finished the match with 25 winners, while he was also excellent at the net, helping him claim his first quarter-final appearance at an ATP Masters 1000 event this season.

Medvedev sent down 5-1 aces but only managed a 54 per cent first-serve percentage, while he also faced 10 break points across the match. Dimitrov won five games in a row to claim the second set.

"I don't remember myself losing three service games, even four service games ever, I guess, on hard courts," Medvedev said.

"That shows how slow this court is and the conditions, more like clay, I would say, which I don't like, because to lose serve four times is just unacceptable."

Dimitrov will face eighth seed Hubert Hurkacz in the quarter-finals after he got past Australian Open semi-finalist Aslan Karatsev 6-1 6-3.

Medvedev added: "Grigor played [the] second part of the match better than anybody did against me [at the] US Open that I won. Playing this level, I don't see him losing to anybody, but let's see the result."

ZVEREV MAKES STATEMENT WITH MONFILS WIN

Olympic Games gold medallist Zverev bulldozed his way past 14th seed Gael Monfils 6-1-6-3 en route to the last eight.

German star Zverev claimed his 20th win from his last 21 matches, needing just over an hour to dispatch Monfils.

Zverev claimed 19 of 25 points at the net, hitting 19 winners including 11 with his forehand, while converting four of eight break points.

"I felt well on the court today. Gael is someone I haven't beaten before, so I knew had to play my best tennis and I definitely was not far away," Zverev said during his on-court interview.

Zverev will take on American 31st seed Taylor Fritz, who defeated 10th seed Jannik Sinner 6-4 6-3.

TSITSIPAS OUTLASTS DE MINAUR

French Open runner-up Tsitsipas saw off a tough challenge from Australian Alex de Minaur to secure his spot in the quarter-finals 6-7 (3-7) 7-6 (7-3) 6-2.

Tsitsipas fought back from a set down to win against the 22nd seed, triumphing in two hours, 43 minutes.

Greek star Tsitsipas showed grit to outlast the tiring De Minaur and will face 29th seed Nikoloz Basilashvili after he knocked off fellow seed Karen Khachanov 6-4 7-6 (8-6).

"That was incredible the way I just stayed in the match," Tsitsipas said. "I had to go through so many difficulties in order to find a solution and I executed towards the end of the match."

There were further top-10 casualties, with sixth seed Casper Ruud also bowing out 6-3 6-3 to 11th seed Diego Schwartzman, who will meet Cameron Norrie in the quarters.

Top seed Daniil Medvedev made quick work of Mackenzie McDonald in his opening match at the Indian Wells Masters, cruising to a 6-4 6-2 victory on Saturday.

Medvedev – the US Open champion – has lost only three of his last 41 sets, and has never dropped one to McDonald in five career meetings with the American as he maintained his red-hot form. 

Russian star Medvedev is now 37-5 on hardcourts this year and appears well-positioned to make it past the third round of the ATP Masters 1000 tournament for the first time as he awaits Filip Krajinovic.

"I'm actually really pleased, because usually I haven’t played well in Indian Wells and I haven’t been playing that well in practices before [the tournament]," Medvedev said in his on-court interview. "[I am] really happy with my performance. That’s the most important [thing] no matter how I played before the tournament."

RUBLEV ROLLS PAST TABERNER

Medvedev's countryman Andrey Rublev closed out the night session with a 6-3 6-4 defeat of Carlos Taberner, who was facing a top-10 opponent for the first time. 

Fourth seed and world number five Rublev won 66 per cent of points on his first serve and hit 30 winners to Taberner's 12. 

Rublev improved to 47-16 this season, 31-9 on hard courts, and will face Tommy Paul in the third round. 

SHAPOVALOV WINS IN NEAR-WALKOVER

Most of the seeded players in action had an easy time of it, none more so than Canadian ninth seed Denis Shapovalov.

Shapovalov's opponent and countryman Vasek Pospisil retired with an apparent back injury after dropping the first three games of the match. 

Sixth seed Casper Ruud blew past Roberto Carballes Baena 6-1 6-2, while eighth seed Hubert Hurkacz downed Alexei Popyrin 6-1 7-5. 

Diego Schwartzman had to work harder to advance, the 11th seed outlasting qualifier Maxime Cressy 6-2 3-6 7-5. 

Top-ranked American Reilly Opelka, the 16th seed, beat Taro Daniel 7-5 6-3 for his first main-draw victory at Indian Wells in four attempts. 

Daniel Evans also went the distance to defeat Kei Nishikori 4-6 6-3 6-4, while former world number three Grigor Dimitrov, 2021 Australian Open semi-finalist Aslan Karatsev and Frances Tiafoe were among the other players to advance.

Cameron Norrie and Casper Ruud will meet in the San Diego Open final after top seed Andrey Rublev and Grigor Dimitrov were beaten.

There was an upset at the ATP 250 tournament, where Russian star Rublev fell to Norrie 3-6 6-3 6-4 in San Diego on Saturday.

Norrie clinched his third career top-10 win as the Brit looks to secure his second ATP Tour-level title on Sunday.

"It's nice to get some revenge. He beat me easily last time, so it's good to see I've improved a little bit," said Norrie, who lost to Rublev in St Petersburg last year.

Standing in Norrie's way is second seed Ruud, who saw off former world number three Dimitrov 6-4 4-6 6-4.

Norway's Ruud – ranked 10th in the world – has the chance to win his fifth title of the season, the most of any player on the ATP circuit.

Norrie holds a 41-19 win-loss record in 2021 and the 26-year-old added ahead of Sunday's decider: "I'm just trying to enjoy today and then I'll try to rest up and get ready for [the final].

"I've been watching both of them this week and they've been playing some of their top level. I'm looking forward to that one tomorrow."

Andrey Rublev needed almost two hours but his punishing forehand helped him to victory over Diego Schwartzman in the San Diego Open quarter-finals on Friday.

Top seed Rublev won 6-1 7-5 in one hour and 52 minutes over the Argentine, who kept on coming throughout the contest.

The Russian world number five's victory books his spot in the last four where he will face Briton Cameron Norrie, who upset fourth seed Denis Shapovalov 6-3 6-1.

Rublev is featuring in his eighth semi-final of the calendar year and chasing his first title since winning in Rotterdam in February.

He had been a break up in the second set after dominating the first, but Schwartzman broke back.

The second set appeared destined for a tie-break with Schwartzman up 40-0 on serve at 5-6, before Rublev won the next five points to claim victory.

"The second set was very tough and enjoyable for the spectators to watch," Rublev said. "Every game was really tough with amazing points and the set could have gone either way."

Second seed Casper Ruud defeated Lorenzo Sonego 6-1 6-4 to book his semi-final spot where he will meet Grigor Dimitrov who beat Aslan Karatsev in three sets.

Ruud's win improved his 2021 record to 45-12, with the 22-year-old Norwegian rising to a ranking of 10.

Andrey Rublev needed almost two hours but his punishing forehand helped him to victory over Diego Schwartzman in the San Diego Open quarter-finals on Friday.

Top seed Rublev won 6-1 7-5 in one hour and 52 minutes over the Argentine, who kept on coming throughout the contest.

The Russian world number five's victory books his spot in the last four where he will face Briton Cameron Norrie, who upset fourth seed Denis Shapovalov 6-3 6-1.

Rublev is featuring in his eighth semi-final of the calendar year and chasing his first title since winning in Rotterdam in February.

He had been a break up in the second set after dominating the first, but Schwartzman broke back.

The second set appeared destined for a tie-break with Schwartzman up 40-0 on serve at 5-6, before Rublev won the next five points to claim victory.

"The second set was very tough and enjoyable for the spectators to watch," Rublev said. "Every game was really tough with amazing points and the set could have gone either way."

Second seed Casper Ruud defeated Lorenzo Sonego 6-1 6-4 to book his semi-final spot where he will meet Grigor Dimitrov who beat Aslan Karatsev in three sets.

Ruud's win improved his 2021 record to 45-12, with the 22-year-old Norwegian rising to a ranking of 10.

Andy Murray's stay in San Diego was short-lived, as the veteran fell to second seed Casper Ruud in straight sets Thursday. 

World number 10 Ruud prevailed 7-5 6-4 over the three-time grand slam winner, rolling to victory after a shaky start. 

Murray broke Ruud in the 22-year-old's second service game of the match, but could not maintain the advantage as Ruud converted five of six break points in the match. 

Ruud will face ninth seed Lorenzo Sonego, who defeated Sebastian Korda 6-4 6-3, saving six of seven break points against his own serve while converting all three of his chances on Korda's. 

Fourth seed Denis Shapovalov defeated Taylor Fritz 7-6 (9-7) 6-2, saving six set points in the process. 

The Canadian moves on to a quarter-final meeting with Cameron Norrie, who downed Daniel Evans 7-6 (7-3) 6-3. 

Grigor Dimitrov dominated August Holmgren 6-1 6-1 in 56 minutes, winning 83 per cent of his service points.

Dimitrov next faces Aslan Karatsev, who rallied to upset fifth seed Hubert Hurkacz 5-7 6-4 6-2. 

Former world number one Andy Murray earned a second-round clash with Casper Ruud at the San Diego Open after easing past lucky loser Denis Kudla in straight sets.

Murray – a three-time grand slam champion – defeated Kudla 6-3 6-2 in just over an hour, winning an outstanding 28 of 31 (90 per cent) first-serve points on Tuesday.

The 34-year-old Murray was also on top on return, converting three of four break-point opportunities against Kudla, to complete a comprehensive display.

Murray – currently ranked 116th in the world – will face second seed Ruud next at the ATP 250 tournament.

Elsewhere, Grigor Dimitrov was made to work for his 6-3 1-6 7-5 victory over Hungarian Marton Fucsovics.

Former world number three Dimitrov triumphed in two hours, seven minutes, confirming a spot in the second round, where he will face US Open semi-finalist Felix Auger-Aliassime.

Diego Schwartzman – the sixth seed – progressed with a 6-2 6-3 win over Italian qualifier Federico Gaio.

Young American Sebastian Korda beat Tommy Paul 6-3 5-7 6-1 in more than two hours, while ninth seed Lorenzo Sonego, Cameron Norrie and Lloyd Harris were also victorious.

Fifth seed Matteo Berrettini survived an early scare on his return from a thigh injury to progress in the second round of the Western and Southern Open in Cincinnati over Albert Ramos-Vinolas on Tuesday.

The Italian world number eight, making his ATP Tour return since losing the Wimbledon final to Novak Djokovic in July, won 6-7 (5-7) 6-3 7-5.

The Spaniard claimed the first set in a tie-break but Berrettini hit back, sending down 25 aces for the match, winning 84 per cent on his first serve.

"I'm happy for the win. I think I served really well," Berrettini said. "My strokes from the baseline weren't working the way I wanted them to, but I knew from the beginning it's been a long time since I played a match, especially on hard, so I expected to feel a little bit weird."

The match extended to two hours and 20 minutes, with the Italian utilizing his backhand slice in the final set to get the edge.

Berrettini, who has a 33-7 record for the season, will face 12th seed Felix Auger-Aliassime or Karen Khachanov in the third round.

"I'm really happy that I'm going to have the chance to play another match because that's what I need," Berrettini said. "I need to play matches. I need to get in the best shape possible."

Canadian sixth seed Denis Shapovalov suffered a shock early upset, going down to France's Benoit Paire 6-3 4-6 7-5 in the Round of 64.

Former US Open, Wimbledon and Australian Open semi-finalist Grigor Dimitrov toppled 13th seed Roberto Bautista Agut 6-3 6-4 in one hour and 21 minutes.

Fellow seed Cristian Garin also bowed out, losing 4-6 6-3 6-4 to qualifier Tommy Paul, while ninth seed Hubert Hurkacz defeated Alejandro Davidovich Fokina 6-1 6-7 (3-7) 6-1.

Marin Cilic, John Isner, Sebastian Korda, Gael Monfils, Reilly Opelka, Lorenzo Sonego and Frances Tiafoe were the other Tuesday winners.

Isner sent down his 13,000th career ace in his three-set win over Briton Cam Norrie.