Alexander Zverev saved two match points 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 match points at 6-5 and 10-9 down 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.
The previous latest ATP finish time was Lleyton Hewitt's 2008 Australian Open clash with Marcos Baghdatis, which ended at 04:34 local time.
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.
Swiatek keeps Poland's hopes alive in Billie Jean King Cup
Iga Swiatek levelled the score for Poland against Czechia, keeping their hopes of reaching the semi-final of the Billie Jean King Cup alive.
The world number two had to dig deep for the win though, triumphing 7-6 (7-4) 4-6 7-5 in two hours and 41 minutes in the second of Poland's singles matches on Saturday.
In their earlier match, Marie Bouzkova had put Czechia ahead but also had to go the distance to beat Magdalena Frech.
It means their quarter-final tie will be decided by doubles, which Swiatek will also play – her first doubles match at the Billie Jean King Cup since 2019 – as they aim to try and win the title for the first time.
The winner of that tie will face Italy in the semi-final, with Jasmine Paolini leading them into the final four.
Japan had taken the lead in the best-of-three tie thanks to Ena Shibahara's win over Elisabetta Cocciaretto, but the French Open and Wimbledon runner-up turned things around.
She beat Moyuka Uchijima 6-3 6-4 in straight sets to level the tie before pairing up with Sara Errani, three months after their Olympic gold triumph, to complete the comeback.
Italy has won the competition four times previously but are looking to better last year's result when they fell to Canada in the final.
ATP Finals: Sinner eases past Ruud to set up title clash with Fritz
Jannik Sinner cruised into the title clash of the ATP Finals after brushing aside Casper Ruud 6-1 6-2 in the semi-finals in Turin.
Sinner, ranked number one in the world, will now face Taylor Fritz in his bid to win his first ATP Finals crown after the American shocked Alexander Zverev in the other semi-final on Saturday.
The Italian was straight into attack against the sixth seed on Saturday, breaking serve in the second game before taking the first set in half an hour, with the home crowd cheering him on.
Sinner did not afford the 25-year-old much success in the second set either, going on a five-game winning streak to progress to the title showdown by hardly breaking a sweat.
On the showpiece match, Sinner said: "We [Taylor Fritz] already played in the round-robin format and will play again in the final.
"I just try to play the best I can [on Sunday]. Anything can happen. I'm just happy to be back here. I've grown as a player since last year.
"It's been a very positive week and year, so I'm really happy."
Sinner had overcome Novak Djokovic in the round-robin stage in the last edition of the tournament but went on to lose to the Serbian in the 2023 final.
He will now hope to buck the trend and claim his maiden crown against Fritz, who he beat in straight sets in the group stage on Tuesday.
ATP Finals: Fritz stuns Zverev to reach year-end showpiece match
Taylor Fritz dumped Alexander Zverev out of the ATP Finals with an entertaining 6-3 3-6 7-6 (7-3) semi-final win, teeing up a final meeting with Jannik Sinner or Casper Ruud.
Fritz became the first American to reach the final of the season-ending event since James Blake in 2006, standing firm in the face of Zverev's monstrous serve to earn a hard-fought win.
Zverev had not seen his serve broken in straight-sets wins over Andrey Rublev, Ruud and Carlos Alcaraz in the group stage, but Fritz achieved that feat in the sixth game to inch ahead in the opener, then only dropped one point in his subsequent two service games.
Zverev came battling back in the second set, breaking at the second attempt then coming through a tough seventh game to hold as he levelled the contest.
However, Fritz would come on strong again in the decider, which required a tie-break after an excellent display of serving from both players. Fritz capped the contest in style on his second match point, sending a fine forehand whizzing across the court and beyond Zverev.
The American, who began the tournament as the fifth seed among eight players, will now have a chance to win the biggest title of his career on Sunday.
Data Debrief: Second time lucky?
This has truly been a breakout season for Fritz, who is the first United States-born player to reach the finals of the US Open and ATP Finals in a single calendar year since Andre Agassi in 1999.
He was beaten in straight sets by Sinner at Flushing Meadows, but he could get a chance for revenge if the Italian overcomes Ruud later on Saturday. Sinner leads the all-time head-to-head with Fritz 3-1.
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