Alex de Minaur has missed out on a rare chance to beat Novak Djokovic twice in the same season, serving up a mistake-riddled display just when the world No.1 looked vulnerable in their Monte Carlo Masters quarter-final.
De Minaur, who had started his year by ending Djokovic's 43-match win streak in Australia at the United Cup, will be cursing himself that he couldn't quite deliver his 'A game' again as he succumbed 7-5 6-4 over two long, draining sets on Friday.
Djokovic wasn't at his sharpest, looked a little ring-rusty and weary in a physically demanding clay-court slog but his big-match nous still proved too much as he set yet another record by reaching his 77th semi-final in a Masters 1000 event, edging him past the mark he'd shared with Rafael Nadal.
There were moments when de Minaur, the first Australian to get this far in Monte Carlo since Mark Philippoussis 25 years ago, had the great man scrambling.
But after making it a brutal slugfest - in the opening set, he'd left Djokovic bending over wearily with hands on knees after winning a draining 34-stroke rally - de Minaur let himself down with lapses of concentration at the end of the first set and regularly in the second.
At the end of their curiously patchy two-hour four-minute battle, which had featured no less than seven breaks of serve alone in the second stanza, de Minaur told his conqueror at the net that it had been an "ugly" affair.
"In the second set I think it was," agreed Djokovic. "We didn’t really play at a high level, we made a lot of unforced errors, there were a lot of consecutive breaks of serve - but a win is a win and I’m glad to go through.
"It was tough for both off us. Alex is one of the quickest players on tour who gets a lot of balls back that normally 99 per cent of players on tour don’t, and he surprised me with some passing shots, particularly in the second set."
But nobody has been able to beat Djokovic twice in succession in the same season since Dominic Thiem five years ago, and de Minaur wasn't quite up to that fiendish task, failing to become the first Aussie semi-finalist in Monte Carlo since John Alexander in 1979.
Two-time winner Djokovic, back in the Monte Carlo semis for the first time since 2015, will meet Casper Ruud in Saturday's semis in a rematch of last year's French Open final after the Norwegian beat France's Ugo Humbert 6-3 4-6 6-1.
Earlier, Australian Open champion Jannik Sinner overcame his first test of the week against Holger Rune to make the semis for the second straight year and set up a mouth-watering battle with two-time champion Stefanos Tsitsipas.
Rune saved two match points en route to winning the second-set tiebreaker, but Sinner responded to win 6-4 6-7 (6-8) 6-3 for his 25th win in 26 matches in 2024.
Tsitsipas eased into the last-four by defeating Karen Khachanov 6-4 6-2, and looked in fine form as he declared: “I would lie if I said it doesn’t bring good memories stepping out on this court."
