Big-serving John Isner bid farewell to his professional career after losing 3-6 4-6 7-6(3) 6-4 7-6(7) to fellow American Michael Mmoh in the US Open second round on Thursday before dropping his final doubles match later in the day.
Isner added 48 more aces to his record tally, starting strongly to win the first two sets before the physical nature of the contest took its toll on the towering 38-year-old.
Mmoh, 25, grew in confidence after winning the third set tiebreak and rode an early break in the fourth set to force a decider.
Isner had match point at 5-4 in the fifth but Mmoh was able to serve his way out of trouble and levelled with a drop shot.
Fittingly for Isner, who was involved in the longest professional match ever, his final set came down to a tiebreak and a stick volley at the net gave him a 4-2 lead that brought the crowd to their feet.
Mmoh refused to back down, however, completing the comeback when Isner's shoestring volley landed in the net.
"Yeah, it's tough. I like to think I work as hard as I can," an emotional Isner said during an on-court interview before his voice trailed off with emotion.
"This is why I worked as hard as I have my whole life to play in atmospheres like this and of course I may not win them all as we know, just like today," he added.
"But to play in front of this crowd and have the support I had is pretty special so thank you."
Isner said he hopes to be remembered as a competitor on the court and a respected presence in the locker room.
"Tennis, it's been a huge part of my life," he told reporters while tearing up.
"It's tough to say good-bye. It's not easy. But eventually this day would come," said Isner, who has four children with his wife Madison.
"Most importantly, man, I have an amazing life and look forward to every second of that going forward."
After a successful college career at Georgia, Isner turned pro in 2007 and went on to reach a career high of world number eight. He won 16 singles titles, the biggest being the Miami Open crown in 2018, his most successful season.
He won the longest professional tennis match in history against Frenchman Nicolas Mahut at Wimbledon in 2010, which lasted 11 hours and 5 minutes and took place over three days.
The All-England Club was also the site of his best result at a Grand Slam tournament, reaching the semi-finals in 2018. He twice made the US Open quarters, in 2011 and 2018.
Isner finishes his 17-year pro career with 14,470 aces, a record that is unlikely to be broken anytime soon.
In the afternoon, Isner and fellow American Jack Sock, who also announced he would retire after the tournament, fell 6-2 3-6 7-6(3) in their first-round doubles match against Albano Olivetti and Robert Galloway.
US men are looking to end a 20 year Grand Slam singles drought at the year's final major and despite war horse Isner bowing out, they are off to a promising start.
Seeded Americans Taylor Fritz, Frances Tiafoe and Tommy Paul are all safely through to the third round with Mmoh and 20-year-old Ben Shelton joining them.