High-flying Alex de Minaur will aim to topple world No.1 Novak Djokovic for the second time this year after the pair booked a fascinating date in the quarter-finals of the Monte Carlo Masters.
While Djokovic will be playing in his 10th quarter-final at the prestigious clay-court tournament on Friday, de Minaur will be the first Australian to play in the last-eight at the Monte Carlo Country Club for a quarter-of-a-century following his 6-3 6-4 victory over compatriot Alexei Popyrin.
It's an intriguing clash with de Minaur thrilled to get the chance to earn another victory following his triumph at the United Cup in January when he ended Djokovic's 43-match, six-year unbeaten streak in Australia while the Serb was bothered by a wrist problem.
Djokovic, still seeking his first tournament win of the year after reaching the semi-finals in the Australian Open, again didn't look at his supreme best on Thursday but was able to avenge his defeat to Lorenzo Musetti in Monte Carlo in 2023 by beating the talented Italian 7-5 6-3.
In his first tournament since splitting with his coach Goran Ivanisevic, Djokovic was outplayed early on but showed that uncanny ability of raising his game when most needed as he converted five of his six break points.
He was also, in familiar fashion, spurred on by the Court Rainier III crowd giving him the bird when he complained about a line call, sarcastically conducting them with a smile as they booed him.Â
"The little exchange with the crowd was the turning point. Ever since then, I started to gain momentum, I think he dropped his level and focus a little bit," Djokovic said.
"I don't think I am still at my top level but it was a great test today against a great player."
Earlier, de Minaur's victory on Court des Princes made him the first Australian since Mark Philippoussis in 1999 to get this far in the prestigious clay-court event.
De Minaur and Popyrin had shared wins in their previous two encounters, but the Aussie No.1 asserted himself with an excellent performance in which he made just three unforced errors and broke the big server's delivery four times.
De Minaur's one stumble came as he served for the match only for world No.46 Popyrin, who had stunned the reigning champion Andrey Rublev in the previous round, to demonstrate plenty of defiance as he converted his sole break point.
It was to prove only a brief respite, though, as de Minaur immediately responded to earn the match-winning break and clinch a victory which looks likely to push the world No.11 back into the top 10 next week.
Karen Khachanov also advanced to the quarter-finals with a 6-3 7-5 win over his Russian friend and compatriot Daniil Medvedev, who for the second day running got involved with a heated exchange with the chair umpire over an erroneous line call.
He'll next face Stefanos Tsitsipas, who defied a spirited second-set comeback from Olympic champ Alexander Zverev before downing the German 7-5 7-6 (7-3).
Jannik Sinner continues to sweep all before him, the Australian Open champ beating Germany's Jan-Lennard Struff 6-4 6-2 to move effortlessly into the last-eight where he'll meet Holger Rune, victor over Bulgaria's Grigor Dimitrov in a gruelling affair 7-6 (11-9) 3-6 7-6 (7-2).
Norwegian Casper Ruud also reached the last eight after beating Hubert Hurkacz 6-4 6-2 and will meet French 14th seed Ugo Humbert,Â
