Novak Djokovic ruined Roger Federer's ambitions of a 100th career title as he outlasted his great adversary 7-6 (6), 5-7, 7-6 (3) in an epic Paris Masters semifinal that stretched his remarkable unbeaten run to 22 matches Saturday.
The only previous time they had met, Djokovic crushed the Russian in straight sets at Wimbledon and, briefly, it seemed as if the same fate could await Khachanov again as he was out-rallied to go 3-1 down in the opening set.
Khachanov won the first set after breaking Djokovic's serve at 5-5 in the first set. The victory required just one break in each set, 6-4, 6-4, and 79 minutes-which was just as well, given that the clock was approaching 11pm and his semi-final against Djokovic begins at 4.30pm Saturday.
Djokovic was a firm favourite to match Rafael Nadal's record tally of 33 ATP Masters 1000 titles, but Khachanov outlined his promise by coming from a break down to secure a 7-5 6-4 victory.
Russia's Karen Khachanov celebrates his first Masters triumph following a memorable win over Novak Djokovic.
The Russian dominated the match and won the first set 6-4.
"Karen played really well and he deserved to win", Djokovic said. "But I played really well".
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"Next to the match I played against (Rafa) Nadal in the Wimbledon semis, this was definitely the most exciting match I've played this year, and probably the best quality match that I was part of".
Federer fended off two more break points to open the third set as Djokovic hit the deck when his ankle appeared to catch in the surface.
"I'm very, very happy and proud about it. I know I have fans here, I can't complain", Federer said.
He rose to a career-high No3 in the rankings in January, and has won at least one title for the last 11 years. Federer's down the T serve was returned well by Djokovic straight in the middle and the Swiss ace took his time before whipping it to Djokovic's right to what looked like a sure victor.
Thiem joined Djokovic and Federer in the Nitto ATP Finals field when Kei Nishikori lost on Friday. And what more can I ask for? "This match could have gone either way", said Djokovic. Five months ago, it was highly improbable considering my ranking and the way I played and felt on the court. But already an established player, a top player.
"I would like to give a lot of respect to Karen for playing such fantastic match today and he deserves to win".