Monte Carlo | Tsitsipas and Ruud take out the world’s top two.

In what proved to be a remarkable day at the Rolex Monte Carlo Masters, both the world’s top two players — who were expected to reach Sunday’s final — surprisingly crashed out of the event thereby dashing all predictions and preventing the eagerly anticipated generational clash between the world number one and two.

No one knows how long he plans to play for, but obviously he’s getting older, but he’s still physically in good shape and playing fantastic tennis. But it’s always fun to play against him, because, you know, it’s one of the toughest challenges in our sport Casper Ruud

Stefanos Tsitsipas opened the day’s proceedings with a two-hour, 40-minute battle to defeat the season’s best player Jannik Sinner, the second seed, 6-4 3-6 6-4, his second loss of the year in five events.

And then Casper Ruud in the second semi-final, required two-hours and 17-minutes to eventually dispatch the 24-time grand slam champion and top seed Novak Djokovic, 6-4 1-6 6-4 heaping more frustration on the great Serbian experiencing his worst start to a season.

The 25-year-old Greek, champion of 2021 and 2022, looked comfortable and despite the Italian’s comeback in the second set, held his nerve and focus to claim an impressive victory to reach his third Monte Carlo final.

Whether Sinner was suffering from mental fatigue following his gruelling quarter final win over the young Dane Holger Rune the previous day, is hard to tell but the power of Tsitsipas’ serving certainly had him on the defensive in the opening set.

However, he has now become renown for his coolness and turned the match around and in the second he looked to be on the way to the final, especially as he broke and held to lead 4-2 in the decider.

With little time left to respond to Sinner’s surge, Tsitsipas dug deep and pressed his rival hard and raised a break-back point only for Sinner to defend robustly, battling back to deuce three times before conceding his serve.

That moment proved crucial for both players as Tsitsipas’ confidence just grew and Sinner’s dropped off for the Greek world No.12 wrapped it all up in the next two games.

“It was tennis at its highest level that I have been able to play. Jannik was an extremely difficult opponent, and it can be seen throughout the year so far. He has been very consistent and I could see that throughout today with his game,” Tsitsipas said following his very impressive performance.

The two rivals Stefanos Tsitsipas and Jannik Sinner shake hands after their semi-final match

(Photo by Julian Finney/Getty Images)

“He is one of the toughest opponents I have faced so far and to find ways when there weren’t that many, I am proud of that. He gave me a very difficult game and [the] way I overcame it is true excellence.”

There was disappointment in the crowd which held a very large number of Italian supporters who were left to digest what they had just witnessed – their hero suffering a rare defeat – not realising that there was more to come.

Casper Ruud enjoys his first victory over Novak Djoovic

(Photo by Jean Catuffe/Getty Images)

Again, the focus was mainly on the world number one Djokovic who has not had the best season of his career so far.

The Serbian, another two-time champion (2013 and 2015) looked to be on the road to correcting that by reaching the semi-finals without dropping a set and he was facing an opponent he had beaten in their five previous encounters.

Surprisingly, he hasn’t won a title since last year’s US Open and so far this year has only played in four events where he has won 11 matches including five at the Australian Open where he made the semis and lost to Sinner.

But one shouldn’t take away from Ruud’s performance. He prepared himself well by playing Estoril the week before and even on the eve of the match, he openly admitted it would be a ‘David and Goliath’ style of clash. He is also an experienced clay-court player with nine 250-level titles to his name and has made the finals of the French Open twice. So far though, he has not pocketed one of the bigger titles.

Ruud put his win, the biggest of his career, in perspective when he commented: “Obviously Novak is Novak. He’s human. Sometimes he doesn’t seem like it, but he is like everyone else.

“I think what really motivated me and helped me a bit today was maybe that I thought about, you know, he lost a match in Indian Wells to Luca Nardi, and he showed there that he’s also vulnerable sometimes. Not many times in a year, but a few days here and there he’s possible to beat.

“If you see that someone has done really well in the beginning of the year, it’s tough to play them, because you’re expecting, wow, this guy is almost impossible to beat. But if you see that many or other players have beaten him before, you believe a bit more in yourself also.”

Adding “In my eyes, [Djokovic is] of the all-time players to try to beat. Today I was able to do it. Something I can remember for the rest of my life and tell hopefully my kids in the future and my grandkids when I’m getting old that, you know, I beat Novak one time at least.

“No one knows how long he plans to play for, but obviously he’s getting older, but he’s still physically in good shape and playing fantastic tennis. But it’s always fun to play against him, because, you know, it’s one of the toughest challenges in our sport.”

Novak Djokovic congratulates Casper Ruud

(Photo by Jean Catuffe/Getty Images)

As Ruud intimates, Djokovic’s invincible mantra is slipping and with a batch of hungry next generation players pushing hard, his time at the top may well be on the wane.

His confidence in his ability remains,

“I’m used to really high standard in terms of expectations of the results, so not having a title is, maybe comparing to the last 15 years, not a great season at all,” Djokovic said.

“But I had semis of Australia, semis here. I only played three tournaments this year, so of course, you know, it’s normal to expect that you have some seasons where you don’t start well, and this is the one.

“Hopefully, yeah, I can pick up, in terms of results, I can build from here, because, you know, I played some good tennis. Hopefully in the next tournaments I’ll be able to play even better.”

This is not Djokovic’s worst start to a season – far from it. In 2018 he did not win a title until Wimbledon but given how much is expected of the GOAT, his uninspiring start has been noted by many, not least the way he lost on Saturday – with a double fault on match point.

“Of course, I’m disappointed, you know, to lose a match like this,” Djokovic admitted.

“I had my chances, but yeah, last game was not great. Unforced errors and he was solid I think until the last shot and deserved to win. My game was kind of up and down.

“I mean, the positive thing is that I kind of managed to come back after losing the first set and really find the strength in the game. So, there are positives to take away from this tournament, for sure, but of course disappointed with the loss.”

Following those results, fans will now be expecting a high-quality final. Can Tsitsipas make it three or will Ruud finally pick up big title.