Novak Djokovic’s latest attempt at winning a 100th ATP Tour title has ended at the first hurdle.
The fifth seed was stunned in straight sets in his opening match at the Monte Carlo Masters, falling 6-3, 6-4 to world No 32 Alejandro Tabilo.
Victory for Tabilo extends a significant run in Monte Carlo for the Chilean, who battled past another former champion – Stan Wawrinka – in the first round.
And, it also maintains his perfect record against Djokovic.
Tabilo has played the former world No 1 twice and has won both times, making him one of just three men to play Djokovic multiple times – and never taste defeat.
Alejandro Tabilo (2-0)
Former world No 19 Tabilo has faced Djokovic on clay the past two years – and has beaten the Serbian on both occasions.
The Chilean dominated Djokovic when they met at the Italian Open last May, breezing past the six-time Rome champion with a 6-2, 6-3 third-round victory over the then-world No 1.
Despite that, Tabilo was a significant underdog heading into this clash; he had a disappointing 3-9 record for 2025 before this match, while Djokovic came in off reaching the Miami Open final.
However, in a match not too dissimilar from their Rome encounter almost 12 months ago, Tabilo made a flat Djokovic pay with another impressive straight-sets victory.
Marat Safin (2-0)
Perhaps the least surprising name on this list is Safin, a former world No 1 and two-time Grand Slam champion at the peak of his powers.
The Russian won the second of his two Grand Slam titles at the Australian Open in 2005 – and beat Djokovic on his way to glory.
Having come through qualifying to make his Grand Slam main draw debut, a 17-year-old Djokovic was drawn against Safin in round one – and was thrashed 6-0, 6-2, 6-1.
Three years later, the two met in the second round of Wimbledon – and this time the Serbian was the favourite to win.
Djokovic was the third seed and the reigning Australian Open champion, while Safin had fallen down the rankings.
However, the Russian channelled past glories with a scintillating display, stunning the world No 3 6-4, 7-6(3), 6-2, ultimately going on to reach the last four.
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Jiri Vesely (2-0)
In one of the craziest stats in tennis history, Vesely – a man who has never been ranked inside the top 30 of the ATP Rankings – has a perfect 2-0 record against the 24-time Grand Slam champion.
Much like with Tabilo, one of Vesely’s two wins over Djokovic came in the second round of Monte Carlo.
Nine years ago, Djokovic came into the 2016 Monte Carlo Masters as the reigning champion and as a dominant world No 1 – only to be stunned 6-4, 2-6, 6-4 by the Czech in his opener.
Six years later, the two met for a second time, and once again it was Vesely who proved to be a surprise victor.
The former world No 35 defeated Djokovic 6-4, 7-6(4) in the quarter-final of the Dubai Tennis Championships, the most recent meeting between the two.
Djokovic and Vesely were set to face off in the second round of the 2016 US Open, though the Czech was forced to withdraw pre-match.
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The post The 3 men to hold a 2-0 record over Novak Djokovic: Alejandro Tabilo joins exclusive club appeared first on Tennis365.
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