For eight meetings, Jan-Lennard Struff had found no way past Novak Djokovic. The ninth came at the worst possible moment for the Serb’s hopes of reaching the Nitto ATP Finals. The 36-year-old German edged out Djokovic, seed No. 4, 6-7 (4), 7-5, 7-6 (5) on Thursday evening to reach the quarterfinals of the Swiss Indoors Basel, closing out the match with an ace.

Djokovic had come to Basel knowing he would likely need to reach the final to stay in the race for Turin. He leaves after the second round, stuck on 2,890 points in the Live Race and outside the qualifying places. He will still return to the Top 10 on Monday thanks to his opening win.

The match was decided by one break and two tiebreaks. Djokovic took the first set tiebreak 7-4. Then, with Struff leading 6-5 in the second set, the German broke the only serve of the match to force a decider. The third set also went to a tiebreak, which Struff won 7-5.

Djokovic, ranked No. 12, had won all eight of their previous meetings, including a 6-3, 6-3, 6-2 victory in the fourth round of the 2025 US Open. The defeat also ends his 6-0 run at ATP 500 level this season, which included the Beijing title. He had been bidding to become the oldest quarterfinalist in Basel history, ahead of Jimmy Connors, who reached that stage at 39 in 1991.

Playing in Basel for the first time since 2011, the 2009 champion had opened his week by coming back to beat Frenchman Ugo Humbert 4-6, 6-3, 6-4. Struff, who entered as a special exempt after reaching the Brussels final last week, had beaten qualifier Yannick Hanfmann 6-4, 6-3 in the first round.

The German reaches his 42nd tour-level quarterfinal, his third of the season after Wimbledon and Brussels, and his second in Basel after 2019. It is also his fourth Top 20 win of 2026. He will face Portuguese Nuno Borges for a place in the semifinals.