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.