An inspired Karen Khachanov sensationally halted Novak Djokovic's 22-match winning run to claim the biggest title of his career at the Paris Masters.
Djokovic had not been beaten since Stefanos Tsitsipas knocked him out of the Rogers Cup in August, but the new world number one came unstuck against another rising star on Sunday.
The unseeded Khachanov struck 31 winners in an imperious performance, denying the 14-time grand slam champion a record-equalling 33rd Masters title with a 7-5 6-4 upset in Bercy.
Djokovic beat Roger Federer in a classic semi-final on Saturday, but failed to match the standards he set on a remarkable winning run as Khachanov rose to the occasion in his first Masters final.
The Russian won 76 per cent of points behind his powerful first serve and broke three times, coming from 3-1 down in the first set before going on to win his third title of the season - and a fourth of his career.
Djokovic will replace Rafael Nadal at the top of the rankings on Monday, but was unable to match the Spaniard's tally of Masters triumphs ahead of the season-ending ATP Finals in London.
A fired-up Djokovic let out a roar and pumped his fist after taking a 3-1 lead when Khachanov drilled a backhand wide under pressure, but the underdog was undeterred and broke back immediately.
Khachanov was enjoying himself, prowling around the court with vigour and going a break up at 6-5 after keeping Djokovic at bay with resolute defence before the Serbian netted when a backhand was fired at his feet.
A rasping serve down the tee sealed the set for the 22-year-old, with Djokovic looking flat and in need of inspiration.
The composed Khachanov maintained his momentum, breaking to lead 2-1 when Djokovic put a backhand into the net and showing lightning sharp reactions to put away a volley at the net as he continued to put the favourite under pressure.
Djokovic saved three break points to reduce the deficit to 4-3, but Khachanov did not allow him a sniff of a break back and sunk to his knees to plant a kiss on the court after an errant backhand from the four-time Paris Masters champion secured the upset.
|Anderson rested for final Test|
|Tite applauds Seedorf for Cameroon´s style of play|
|Griezmann not obsessed with Ballon d´Or|
|Neymar feels injury is ´nothing serious´|
|Durant says Green altercation won´t impact his free agency|
|Morris blasts drama surrounding Wizards: It´s messed up|
|Scaloni thrilled for Dybala, Icardi|
|Green´s last-second shot keeps Raptors atop East standings|
|Deschamps praises Griezmann for Giroud gesture|
|Warriors star Curry improving, still out at least three more games|
|Chile 4 Honduras 1: Sanchez, Vidal shine for La Roja|
|Argentina 2 Mexico 0: Icardi, Dybala score first international goals|
|Mickelson calls Tiger the greatest of all time|
|Durant fined $25,000 for using inappropriate language|
|Fizdale isn´t concerned about Knicks´ losing streak|
|No particular concern for Mbappe – Deschamps|
|PSG team-mate Choupo-Moting hopes Neymar injury is not serious|
|McLeish marvels at stylish Scotland´s promotion success|
|Draw proves Poland can play well without Lewandowski – Brzeczek|
|Giggs: Wales let themselves down|
|Sarachan ´moved USA forward´ in interim spell|
|Mickelson lays $200,000 bet with Woods for first hole|
|Dolphins QB Tannehill to start against Colts|
|Murcia edge out Banvit, Bonn crush Opava|
|Neymar injury not serious, says doctor|
|Mancini: Italy ahead of schedule|
|France 1 Uruguay 0: Giroud hits the spot after Mbappe injury blow|
|Portugal 1 Poland 1: Milik penalty salvages precious point as Danilo sees red|
|Italy 1 United States 0: Politano snatches late winner for Mancini´s men|
|Scotland 3 Israel 2: Forrest hat-trick seals Nations League promotion|
|Brazil 1 Cameroon 0: Richarlison fills Neymar´s boots as skipper suffers injury|
|France & PSG star Mbappe suffers shoulder injury|
|Albania 1 Wales 0: Gunter´s night spoiled by Balaj|
|Leeds and Manchester United to meet in friendly|
|Outspoken Smith leaves Cavaliers|
|PSG star Neymar injured for Brazil|
|Juventus midfielder Can back in training after surgery|
|Rams-Chiefs rollercoaster was the NFL´s modern-day masterpiece|
|Ronaldo an AC Milan target in 2017, confirms Fassone|
|Farah could get back on track at Tokyo Olympics|
|PSG still waiting on Alves and Kurzawa|
|Atalanta reject Gasperini to AC Milan speculation|
|Edmonton Oilers name Hitchcock new head coach|
|JR Smith on Cleveland Cavaliers: Tanking ´was always the plan´|
|Chester signs new Wakefield deal|
|F1 Raceweek: Countdown on to Alonso farewell|
|Rain disrupts Lorenzo´s Honda debut|
|VAR a possibility for Champions League knockout rounds|
|FFP vulnerable in areas, says UEFA president Ceferin|
|Sri Lanka draft in uncapped Peiris to replace Dananjaya|
|Coman back in Bayern training but Lewandowski has knee injury|
|Qalandars land De Villiers in PSL draft, Smith second pick|
|F1 changes helped less talented drivers on the grid - Alonso|
|Agnelli: No super league talks since 2015|
|I hope from now on it only gets better - Floersch update on horror crash|
|Calf injury rules Ashton out of Australia match|
|Halfpenny to miss South Africa clash|
|Hard for Lazio to hold on to Milinkovic-Savic, says Lotito|
|Australia´s next generation pay tribute to retiring Cahill|
|Bairstow pushing hard for Test recall|
|Cane eyes 2019 Super Rugby return after neck break|
|Van Dijk finds time to console referee during Dutch delight|
|Cahill sheds tear at end of phenomenal Australia career|
|WATCH: Pelicans coach Gentry interviews himself|
|Where does Chiefs-Rams classic rank among NFL´s highest-scoring matches?|
|Australia 3 Lebanon 0: Boyle bags brace on Cahill farewell|
|Guendouzi underlines desire to represent France|
|I might need a couple of drinks to relax after that! - Rams coach McVay|
|Juventus´ Alex Sandro has Premier League ambition|
|Ederson taking goalkeeping to another level, says City hero Weaver|