Novak Djokovic was eliminated from the Swiss Indoors in the round of 16, falling to Jan-Lennard Struff in a three-set defeat that ended his bid to match Roger Federer's record of 103 career titles and dealt a blow to his chances of qualifying for the Nitto ATP Finals.
The Serbian took the first set 7-6, but the German big hitter claimed the next two 7-5 and 7-6 to advance to the quarter-finals, where he will face Nuno Borges on Friday evening.
Djokovic's run in Basel ends
Djokovic had earlier secured a 4-6, 6-3, 6-4 win over Ugo Umbert on Wednesday, but admitted to feeling rusty at the Basel-based tournament after that match.
He said: "I was under attack from the very first point and had to weather the storm. It's my first indoor match, so I expected to be a little bit rusty in a tough draw. It is a big win for me, I know there are quite a few things I can do better but a win is a win, and I will take that today."
ATP Finals qualification in doubt
The loss means Djokovic will remain one title behind Federer's haul of 103 career titles. It also impacted the 39-year-old's chances of qualifying for the Nitto ATP Finals, as he now trails Rafael Jodar by 319 points in 11th place in the PIF ATP Live Race To Turin.
Jodar's loss to Valentin Vacherot on Thursday had allowed Djokovic to overtake him in ninth, in the event he went on to win the title in Basel. However, the defeat has changed that outlook.
While it remains mathematically possible for Djokovic to qualify, he faces an uphill battle, with the Rolex Paris Masters the only remaining tournament before the seasonal finale. Only the top seven in the rankings automatically qualify, with the eighth place going to a Grand Slam winner ranked between eighth and 20th, or the player who occupies eighth place in the standings.
The current top eight are: Alexander Zverev, Jannik Sinner, Carlos Alcaraz, Ben Shelton, Daniil Medvedev, Flavio Cobolli, Arthur Fils and Frances Tiafoe.