David Goffin beat Novak Djokovic for the first time in his career on his fifth match point, winning 6-2, 3-6, 7-5 to reach the Monte Carlo Masters semifinals on Friday.
Goffin denied Djokovic a possible 50th career match against defending champion Rafael Nadal, who was playing the last remaining quarterfinal against unseeded Diego Schwartzman.
The 10th-seeded Goffin had lost all previous five matches to Djokovic and looked to heading for another when the 12-time Grand Slam winner led 4-2 in the decider.
But Goffin broke him in the eighth game and held firm on his own serve when taken to deuce in a tight 11th game.
The pressure was back on the second-ranked Djokovic to hold and force a tiebreak, but Goffin kept coming at him.
Djokovic saved the first match point with an ace; the second one on his second serve; the third with a stinging forehand winner and a fourth when Goffin chopped a backhand into the net.
But a sloppy unforced error on forehand gave Goffin another chance, and he took it with a deep forehand right on the line that Djokovic swiped back off balance into the net.
Goffin, who had taken just one set off Djokovic before Friday, grabbed his head with both hands.
Djokovic, the champion here in 2013 and 2015, hugged him at the net.
Bopanna, Cuevas reach s/F
Rohan Bopanna and his partner Pablo Cuevas knocked out fifth seeds Raven Klaasen and Rajeev Ram after a three-set battle to progress to the quarterfinals of the ATP Monte Carlo Masters event here.