A tearful Roger Federer bid goodbye to a 25-year career with defeat at the Laver Cup in a doubles contest that went past midnight in London.
Federer teamed with long-time rival Rafael Nadal against American duo Frances Tiafoe and Jack Sock as Team Europe face Team World at the O2 Arena.
After winning the first set, the Swiss and the Spaniard were faced with a spirited fightback from Tiafoe and Sock, who won a second-set tie-break before also clinching the match tie-break to seal victory 4-6 7-6 (7-2) 11-9.
There had been a great atmosphere in London on Friday for the fifth edition of the three-day competition.
Federer, 41, had not played a match since he was knocked out of Wimbledon by Hubert Hurkacz at the quarter-final stage last year due to knee injury.
There were huge cheers when Federer and Nadal came onto the court and loud roars for the Swiss great when he came up with his first winner.
There was a sensational moment in the first set when Federer appeared to have won a point after his shot hit the top of the net and bounced in, only for a replay to show the ball had somehow been hit through a small hole between the net and the post, meaning Team Europe lost the point, despite the remarkably unlikely event of the ball passing through such a gap.
Novak Djokovic and Andy Murray were among Federer and Nadal's team-mates offering some tactical input between games, and the legendary duo had to save a first break point of the match before the Spaniard held to put them 5-4 up.
It was two of the all-time greats that took a tight opening set when Sock put a volley into the net, prompting Team World captain John McEnroe to tell his doubles pair they appeared to be getting "caught up in the hoopla."
A determined Team World managed to level it up after a back-and-forth second set went to a tie-break, with Tiafoe and Sock coming out on top with their superior power and pace.
That took it to a dramatic deciding match tie-break, with every point keeping fans holding their breath, including some trademark Federer magic at 6-7 when he diverted a Sock shot across court for a crowd-pleasing winner.
It looked like the dream script was being followed as Federer served at match point for himself and Nadal, but the former could only hit a shot into the net, before Sock and Tiafoe won the next two points to secure the win for Team World.
It was then hugs all round as respect was paid to the 20-time grand slam winner at the conclusion of a phenomenal career.
Earlier in the day, Casper Ruud drew first blood for the Team Europe, beating Sock 6-4 5-7 10-7, before Stefanos Tsitsipas doubled their advantage with an emphatic 6-2 6-1 defeat of Diego Schwartzman.
There was drama after the first set of that second singles match when a protester, wearing a T-shirt with the message, "END UK PRIVATE JETS" on, set their arm alight on court before being escorted out by security.
Alex de Minaur then got Team World on the board with a 5-7 6-3 10-7 success over home favourite Murray before the late-night main event under the lights.
World number one Swiatek sees off Xiyu in Madrid opener
World number one Iga Swiatek overcame Wang Xiyu with the minimum of fuss on Thursday to progress to the third round of the Madrid Open.
Swiatek has yet to win the title in Madrid, which is the only clay-court European event at which the Pole has not triumphed, but she got off to a flying start with a 6-1 6-4 victory over Xiyu.
"I love this place. I got to know the city a little better last year," Swiatek said. "So this time I feel more comfortable around."
Next up for the 22-year-old is a third-round tie against 27th seed Sorana Cirstea on Saturday.
Data Debrief
Swiatek has registered 150 match wins on the WTA Tour since the start of 2022. Elena Rybakina and Coco Gauff are the next best with 108 wins each.
She also became the first player born this century to claim 50 combined match wins in Madrid, Rome and Roland-Garros, since the inaugural women's singles event at the Madrid Open in 2009.
Dominant Gauff double bagels Rus at Madrid Open
Coco Gauff made a flying start to her Madrid Open campaign on Thursday, recording the first double bagel main-draw win of her career as she cruised past Arantxa Rus to reach the round of 32.
Gauff needed just 51 minutes to see off 33-year-old Rus as she booked a meeting with Ukraine's Dayana Yamstremska for Saturday.
The US Open champion lost just 18 points throughout the match – eight in the opener and 10 in the second set – as she put any doubts over her recent form to bed in emphatic fashion.
Gauff's power proved too much for Rus in the opener, the third seed winning 88 per cent of points behind her first serve and converting three of four break points to go a set up in just 23 minutes.
Rus brought up four break points midway through the second set, but when she failed to convert them, Gauff punished her in ruthless fashion by reeling off another three games then finishing things with a terrific forehand winner.
Speaking after her win, the American said: "I played really well today. It was just one of those days for me… 6-0 6-0, I've never done that before, I'll probably never do it again."
Data Debrief: Gauff matches Azarenka, Halep feat
Gauff is just the third player to register a 6-0 6-0 win in the women's singles draw at the Madrid Open, following in the footsteps of two former world number ones in Victoria Azarenka and Simona Halep.
The American, who only turned 20 last month, is also the youngest player to double bagel an opponent in any main-draw match on the WTA Tour since Iga Swiatek did so against Karolina Pliskova in the 2021 Italian Open final in Rome.
Nadal cruises past teen Blanch to tee up De Minaur rematch in Madrid
Darwin Blanch presented little challenge for Rafael Nadal, who dropped just one game in a convincing 6-1 6-0 triumph at the Madrid Open.
Nadal is feeling his way back to fitness, but 16-year-old qualifier Blanch offered little resistance to the 22-time major champion on Thursday.
Making his farewell appearance at the Madrid Open, where he has won five titles, Nadal needed just 64 minutes to progress to round two.
"I think today I played against an opponent with a great future in front [of him], but today, still making mistakes," said Nadal.
"I just tried to be there, be solid all the time without taking a lot of risks. It worked well. I'm happy to be through and I wish him all the very best for the future."
Nadal's reward is a rematch with Alex de Minaur, who he lost to last week in Barcelona.
Data Debrief
This game saw the largest age gap (21 years, 117 days) between two opponents in the history of ATP Masters 1000 events.
Nadal has now registered 57 wins at the Madrid Open, which is 20 clear of any other player.
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