Novak Djokovic lost to Jan-Lennard Struff in a three-set Basel thriller on Thursday. The 6-7, 7-5, 7-6 defeat stalled the Serbian’s pursuit of Roger Federer’s title record. This result also hurt his ATP Finals qualification hopes. Djokovic now looks toward the Paris Masters to gain points after this tough second-round exit.

Jan-Lennard Struff defeated Novak Djokovic in a three-set Basel thriller. The loss stalled Djokovic's title-record pursuit and dented his ATP Finals qualification hopes.

Novak Djokovic's return to the Swiss Indoors Basel ended in disappointment as the Serbian suffered a dramatic second-round defeat to Germany's Jan-Lennard Struff on Thursday. The 39-year-old went down 6-7 (4), 7-5, 7-6 (5) in a contest lasting two hours and 36 minutes, missing out on an opportunity to add another title to his remarkable collection.

The defeat also means Djokovic will have to wait to close the gap on Roger Federer's tally of 103 career titles. The 24-time Grand Slam champion won his 102nd tour-level trophy at the China Open in Beijing earlier this month. Only Federer, with 103, and Jimmy Connors, who holds the all-time record with 109, have won more singles titles in men's tennis.

There was an added layer of history to Djokovic's Basel campaign. He returned to the tournament for the first time since 2011, having won the title in 2009 by defeating Federer in the final. Federer, who grew up in Basel and lifted the trophy at his hometown event a record 10 times, got the better of Djokovic in the 2010 final. The Serb also reached the semi-finals in 2011.

Struff, ranked 47th in the world, produced an impressive performance to knock out the fourth seed. Djokovic took the opening set in a tie-break, but the German fought back to level the match after converting his first break-point opportunity in the second set. The decider went to another tie-break, where Struff held his nerve before sealing the win with his 27th ace, leaving Djokovic with no chance of a return.

DJOKOVIC'S ATP FINALS HOPES TAKE A HIT

The Basel exit is a significant setback in Djokovic's bid to qualify for the season-ending ATP Finals in Turin. He had an opportunity to gain crucial ranking points with a title run, particularly after Rafael Jodar's earlier defeat opened up a route into the qualification positions. Following the loss, Djokovic trails the Spaniard by 319 points, with the Paris Masters the final tournament before the ATP Finals.

The Rolex Paris Masters, an ATP Masters 1000 event, is scheduled to take place from November 2 to 8. Djokovic is set to return to the tournament after a three-year absence, having won the title a record six times. A strong run in Paris could prove crucial to his hopes of securing a place in Turin.

Meanwhile, top seed Ben Shelton also suffered a shock exit in Basel, losing to Swiss wildcard Jerome Kym, ranked 222nd in the world. The 23-year-old prevailed 6-3, 6-7 (4), 7-6 (1), handing Shelton another defeat against a player ranked outside the top 100 this season. Kym will next face eighth seed Jiri Lehecka in the quarter-finals.