May 26, 2024; Paris, France; Stan Wawrinka of Switzerland returns a shot during his match against Andy Murray of Great Britain on day one of Roland Garros at Stade Roland Garros.

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2025 Misery Continues for Stan Wawrinka as Alejandro Tabilo Sets Up Novak Djokovic Clash at Monte Carlo Masters

Wawrinka has managed only one tour-level win in 2025.

May 26, 2024; Paris, France; Stan Wawrinka of Switzerland returns a shot during his match against Andy Murray of Great Britain on day one of Roland Garros at Stade Roland Garros.

Three-time Grand Slam champion Stan Wawrinka crumbled to a dramatic loss on Monday, as Alejandro Tabilo won 1-6 7-5 7-5 at the Monte Carlo Masters. It was just the third win of the Chilean’s season, and a monumental one at that. The win means that Tabilo will now face Novak Djokovic in Round-2, while Wawrinka faces yet another early exit in his long drawn hunt for form.

Wawrinka, now ranked No. 163 in the world, has had an abysmal start to 2025. The Swiss legend is yet to reach a tour-level quarterfinal since October 2024, and has looked like a shadow of his former self. With age catching up to him, there is no doubt that we are coming towards the fag end of an incredibly glittering career. And the shock loss from a winning position vs Tabilo may be one of the final few icings on the cake.

Stan Wawrinka Forefeits Convincing Lead to Drop Out of ATP Monte Carlo Masters 2025

Wawrinka raced off the blocks on Court Rainier III, unleashing some fearless groundstrokes at the expense of Tabilo. The 40-year-old was making his 15th appearance in Monte Carlo – the fourth highest in the Open Era. Quickly grabbing the opener 6-1, Wawrinka was halfway into giving fans a juicy Djokovic-Wawrinka meeting at the Principality.

Looking for his second tour-level win of the season, Stan began losing gas in the second set. Tabilo targeted the single-handed backhand with aplomb, and began finding his range more often. Searching for his first clay court win on tour since Rome 2024, the 27-year-old won the second set and powered ahead to 5-3 in the decider.

Squandering his lead on multiple occasions, Wawrinka saved a match point to level things up at 5-5. However, Tabilo made it count on the big points and won most of the thunderous exchanges – resulting in him converting his third match point to win 1-6 7-5 7-5.

Tabilo to Face Novak Djokovic in Monte Carlo Round-2

The exhausting win means that Alejandro Tabilo will now face another veteran in the form of Novak Djokovic in Round-2. The Serbian is searching for his 100th title, and has not won an ATP title since the year-end finals in 2023. Nonetheless, he is a two-time winner of the Monte Carlo Masters – an event utterly dominated by the great Rafael Nadal.

Making memories in the ETERNAL CITY 🫶👏

The moment Alejandro Tabilo STUNNED the World No. 1 Djokovic in Rome!!! @InteBNLdItalia | #IBI24 pic.twitter.com/IOlfOColnT
— ATP Tour (@atptour) May 12, 2024

Despite losing eight matches in a row on clay, Alejandro Tabilo dug deep to overhaul Stan Wawrinka. It is worth nothing that he has a winning head to head record against ‘Nole’ too – beating him in Rome 2024 en route to the semifinals. Can he do the same in Monte Carlo? Round-2 action begins on Tuesday.

Alejandro Tabilo

ATP

ATP Masters 1000

Monte Carlo Masters

Novak Djokovic

Rome Open

Stan Wawrinka

Tennis

Sankalp Harikrishnan

A passionate sports fan through and through, I am currently pursuing my MA in Global Sports Journalism. I specialise in tennis and football writing at The Playoffs News, and I have prior experience working at EssentiallySports and Sportskeeda. Born and raised in Bengaluru, India, sport was my safe space right from my childhood. After trying my hand at multiple sports and representing my educational institutions in cricket, badminton and table tennis, I found sports media to be my calling.