Rafael Nadal suffered his second defeat in as many matches after going down 3-6 6-1 7-5 against Alex de Minaur at the United Cup.
The 22-time grand slam champion, who was also beaten by Great Britain's Cameron Norrie in his opening match, is still seeking his first victory of the season with the Australian Open just around the corner.
Home favourite De Minaur delighted the Sydney crowd by recovering from a set and break down to claim his maiden win over the world number two.
"I think it's definitely up there [as one of my best wins]," he said. "It's one of those achievements that you have unlocked in your career.
"But also, it's a big win for myself, one that I really needed. I'm going to cherish and use, take all the confidence from this and be able to hopefully take it to have a good [Australian] summer."
Spain and Australia are unable to progress to the City Finals, but Nuria Parrizas Diaz levelled the Group D tie with a 6-1 6-3 victory over Maddison Inglis.
The USA, who required just two points against Germany to advance to the next stage, set up a showdown with Great Britain after Taylor Fritz and Madison Keys enjoyed straight-set successes over Alexander Zverev and Jule Niemeier respectively.
Italy moved to the brink of joining them in the City Finals after taking a 2-0 lead over Norway. Lorenzo Musetti overcame Viktor Durasovic in straight sets, while Martina Trevisan edged out Malene Helgo in three.
Greece require one win from their final three matches against Belgium to also advance, Stefanos Tsitsipas hit 12 aces on the way to defeating David Goffin 6-3 6-2 to level the Group A showdown at 1-1.
Poland's winner-takes-all Group B clash with Switzerland is also finely poised at 1-1. World number one Iga Swiatek beat Belinda Bencic 6-3 7-6 (7-3), before Marc-Andrea Huesler's 6-3 6-2 victory against Daniel Michalski.
French Open day five: Iga Swiatek eases through as Daniel Altmaier shocks Sinner
Women’s top seed Iga Swiatek eased into the third round of the French Open with victory over Claire Liu.
Coco Gauff set up an intriguing clash with 16-year-old Mirra Andreeva, while Wimbledon champion Elena Rybakina saw off teenage Czech Linda Noskova.
The match of the day saw German Daniel Altmaier defeat eighth seed Jannik Sinner in five hours and 26 minutes, the fifth longest match in tournament history.
Picture of the dayTweet of the dayQuote of the dayStat of the dayChina on the march
China has been a virtually non-existent presence in men’s tennis in the open era but three players featured in the main singles draw and Zhang Zhizhen, who will play Casper Ruud, is the first through to the third round since 1937.
Fallen seeds
Men: Jannik Sinner (8), Tommy Paul (16), Alex de Minaur (18)
Women: Madison Keys (20), Donna Vekic (22)
Who’s up next?
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Cameron Norrie will try to break new ground at the French Open when he takes on talented young Italian Lorenzo Musetti.
The British number one is yet to reach the fourth round at Roland Garros, where he could face top seed Carlos Alcaraz, who plays Denis Shapovalov in the night session.
Novak Djokovic faces Alejandro Davidovich Fokina while Aryna Sabalenka and Jessica Pegula are the leading women in action.
Russian teenager Mirra Andreeva dreams of ‘winning 25 grand slam titles’
Sixteen-year-old Mirra Andreeva said she dreams of winning 25 grand slam titles after reaching the third round of the French Open.
The prodigious Russian talent came through qualifying and has lost just six games in her first two main-draw matches, beating France’s Diane Parry 6-1 6-2 on Thursday.
Andreeva only turned 16 at the end of April and is setting her sights sky high for her tennis career.
“The dream: I know that (Novak) Djokovic, he did 22 grand slams, so I want to go until 25, if it will be possible,” said the confident teenager.
Andreeva will try to keep her feet on the ground, though, adding: “As my coach says, to not be like a diva, to stay humble all the time. I don’t think that I have a lot of success now. I didn’t win any tournaments. I just play. It’s the third round of Roland Garros. I will play.”
Defending champion Iga Swiatek again had a tough first set, this time against American Claire Liu, before pulling away to win 6-4 6-0.
The world number one, who celebrated her 22nd birthday on Wednesday, had difficulty finding her rhythm in windy conditions.
Swiatek would rather play on Philippe Chatrier in the day than at night, though, and revealed she has been requesting not to feature in the late prime-time session.
Every night session so far has consisted of a men’s match despite organisers facing criticism last year for not giving equal billing to the women.
“I felt like I played already night sessions in this clay court swing,” said Swiatek. “Obviously it would be nice if we had women’s matches as well. But I’m not helping.”
Wimbledon champion Elena Rybakina fought off a Czech teenager for the second straight round, following up her success against 16-year-old Brenda Fruhvirtova by defeating 18-year-old Linda Noskova 6-3 6-3.
Seventh seed Ons Jabeur has looked strong so far, the Tunisian seeing off Oceane Dodin 6-2 6-3, while Kayla Day upset American compatriot Madison Keys 6-2 4-6 6-4.
Jannik Sinner knocked out of French Open by Daniel Altmaier after five-hour epic
Eighth seed Jannik Sinner was toppled by German Daniel Altmaier in a five-hour epic at the French Open.
In a tremendous atmosphere on Suzanne Lenglen, Altmaier clinched a 6-7 (0) 7-6 (7) 1-6 7-6 (4) 7-5 second-round victory after five hours and 26 minutes – the fifth longest match in the tournament’s history – having saved two match points when Sinner served for the win in the fourth set.
A tense finale saw Altmaier broken when he served for the match for the first time at 5-4 in the decider and then pegged back from 40-0 at 6-5.
Italian Sinner had three chances to force a deciding tie-break, and chucked his racket to the clay in anger after missing the final one, before Altmaier, ranked 79, took his fifth chance with an ace.
The German, who lost to Sinner in five sets at the US Open, sat in his chair sobbing afterwards, saying: “I love clay and I love the crowd and everything. The emotions were crazy.”
Altmaier, who reached the fourth round on his Roland Garros debut in 2020, next faces Grigor Dimitrov after the Bulgarian’s more straightforward 7-6 (4) 6-3 6-4 victory over Emil Ruusuvuori.
An open bottom half is now even more so, with fourth seed Casper Ruud the highest-ranked player remaining.
The Norwegian appears to be playing himself into form at the right time after a difficult season so far, and said after a 6-3 6-2 4-6 7-5 victory over Giulio Zeppieri: “It was tough to try to finish the match, and it was a two tough sets, but I’m happy to win one of them and be through to the third round.”
Twelfth seed Frances Tiafoe fought back from a set down to defeat Aslan Karatsev 3-6 6-3 7-5 6-2 but 18th seed Alex De Minaur fell in straight sets to Argentina’s Tomas Etcheverry.
Etcheverry next meets 15th seed Borna Coric, who won another five setter against Pedro Cachin, and Thiago Seyboth Wild followed up his upset of second seed Daniil Medvedev by beating Guido Pella 6-3 3-6 6-4 6-3.
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