Jan-Lennard Struff made it ninth time’s the charm after knocking Novak Djokovic out of the Basel Open in the second round on Thursday night.

Heading into the contest, Struff was well aware of his losing 0-8 record against the 39-year-old, whom he declared the greatest player of all time.

He told the ATP, “One is the GOAT, so it’s nice to have the opportunity to maybe play against him. He needs to win his match first, because Humbert is a great player as well. Against Novak, my head-to-head record isn’t that great. But whose head-to-head record is great against Novak? It would be a pleasure to play against him.”

Despite owning their head-to-head, Djokovic was wary of the 6ft 5in German, who is known for his big serve and booming groundstrokes.

He said, “He’s been playing really well lately. He’s always been a tough player on any surface. He’s so tall and has one of the biggest serves. He loves to come in and be another guy who is super aggressive.”

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And so it proved to be as Djokovic edged a tight first set on a tiebreak, before Struff broke the 24-time major winner right at the end of the second to force a decider.

Both players earned and saved break points in the third set, and against the odds, it was the 36-year-old who claimed his first victory over Djokovic in a 6-7 (4), 7-5, 7-6 (5) triumph in two hours and 36 minutes.

In the wake of this result, Djokovic now faces a tall order to qualify for the ATP Finals next month. He is 11th in the Race to Turin with 2,890 points, with Alex De Minaur 40 points ahead of him in 10th.

In light of Jannik Sinner’s season-ending knee injury, the ninth-placed player can qualify for Turin, with Rafael Jodar currently in the last qualification spot on 3,184 points.

Djokovic may find himself slipping down the rankings this week as Taylor Fritz and Tommy Paul could both overhaul him if they have deep runs in Basel and Vienna, respectively.

The Serb will now likely have to win the Paris Masters or go far at the tournament and hope his rivals slip up in the French capital to qualify for the season-ending event. Djokovic had set his sights on qualifying for the ATP Finals but this Struff loss is a real hammer blow.

In regard to his prize money for this week, Djokovic pockets €37,790 (£31,566) and a meagre 50 ranking points. Struff will now face Nuno Borges in the quarter-finals.