Novak Djokovic lost to Jan-Lennard Struff 6-7(4), 7-5, 7-6(5) in the second round of the Swiss Indoors in Basel on Thursday. It was Struff's first win in nine meetings with the Serb, who had won all eight of their previous matches. The 36-year-old German, ranked No. 47, now plays Portugal's Nuno Borges in the quarter-finals.

Struff finished it on his third match point with his 27th ace of the match, according to the Associated Press. Djokovic had saved the second match point with an ace of his own, but could not get a racket on the last serve.

One break across three sets

There was only one break of serve in the whole match, tennismajors reported, and it was Struff's. Djokovic, who played Basel on a wild card and was seeded fourth, won the first-set tie-break 7-4. Struff then broke him in the second set to take it 7-5, which left the score at one set each.

The decider followed the pattern of the first. Both men held serve until a second tie-break, and this time Struff won it 7-5. For a player who has lost to Djokovic so many times, it was a composed finish against one of the best returners in the game.

What both men said beforehand

Struff had been realistic about the numbers before the match.

One is the GOAT, so it's nice to have the opportunity to maybe play against him.

Jan-Lennard Struff, ahead of the match, as quoted by the ATP Tour

Against Novak, my head-to-head record isn't that great. But whose head-to-head record is great against Novak?

Jan-Lennard Struff, on the head-to-head, as quoted by the ATP Tour

Djokovic had been wary of the serve, in comments the ATP published ahead of the meeting.

He's so tall and has one of the biggest serves.

Novak Djokovic, on Struff, as quoted by the ATP Tour

He added that he would have to start better than he had in the first round, when he came from a set down to beat Ugo Humbert, as we covered after that match.

Struff arrived in form. The ATP said he had won five of his previous six tour-level matches, reached his first final since 2024 in Brussels, and made his first major quarter-final at Wimbledon this year.

The Turin race gets harder

Djokovic is chasing a record 19th qualification for the Nitto ATP Finals in Turin. Before the match, the ATP had him 11th in the Race, 319 points behind ninth-placed Rafael Jódar, who held the last qualifying place. Tennismajors said he needed to reach the final in Basel to stay in contention. It put him on 2,890 points, outside the qualifying places, after the defeat.

The result also ends a run that began well. Djokovic won the China Open in Beijing earlier this month, his 102nd tour-level title, which the AP noted is one short of Roger Federer's 103.

Struff's road to the quarter-finals

Struff beat his compatriot Yannick Hanfmann 6-4, 6-3 in the first round on Wednesday, the ATP said. In Brussels, the week before, he reached the final after beating top seed Arthur Fils. Borges, his next opponent, beat Casper Ruud 1-6, 6-3, 6-4 in the first round, and Djokovic had beaten him in the first round in Beijing, as we reported.

A day of upsets in Basel

Djokovic was not the only name to leave. Ben Shelton lost 6-3, 6-7(4), 7-6(1) to the Swiss wild card Jerome Kym, ranked 222nd, who plays Jiri Lehecka next, the AP reported. Arthur Fils beat Alex Michelsen 4-6, 6-3, 7-6(5) and will face Taylor Fritz in the quarter-finals.

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