Novak Djokovic’s 5 worst Monte Carlo Masters defeats: ft world No 32 Alejandro Tabilo

Oli Dickson Jefford 10 Apr 2025 12:08 PM

Novak Djokovic looks on.

Novak Djokovic’s quest for a third Monte Carlo Masters title in 2025 was ended in stunning fashion by Alejandro Tabilo on Wednesday.

Defeat for Djokovic – which he described as “horrible” – continues a challenging run of form for the 24-time major champion at the tournament, having not reached the final since his second triumph in 2015.

Many of the Serbian’s losses at the event since then have come as a huge surprise, with his latest loss to Tabilo among the biggest shocks.

Since 2015, Djokovic has lost five times in Monte Carlo to players ranked outside the top 20.

5) Lorenzo Musetti – world No 21 (2023)

Djokovic has dominated his head-to-head against Musetti, winning eight of his nine matches against the Italian star – including five wins since the start of the 2024 season.

However, Musetti’s one win over the Serbian came in Monte Carlo two years ago.

Producing some of the best tennis of his career, world No 21 Musetti – the 16th seed – rallied from a set down to stun the Serbian 4-6, 7-5, 6-4 in the round of 16 back in 2023.

Djokovic gained revenge by beating Musetti in Monte Carlo the following year, and has not lost to the 23-year-old since.

4) Alejandro Tabilo – world No 32 (2025)

A former world No 19 at his peak, Tabilo has fallen back outside the top 30 after significant struggles with his form in recent months.

Heading into Monte Carlo, the Chilean had not won back-to-back matches since August, and held an underwhelming 3-9 record for 2025 before his match against Djokovic.

However, that did not stop him from picking up a second win in as many meetings against the Serbian, triumphing 6-3, 6-4 on Wednesday.

Tabilo is now one of just three men to play multiple matches against Djokovic and never be beaten by the former world No 1.

3) Dan Evans – world No 33 (2021)

Former world No 21 Evans is not known for his clay-court prowess, which made his stunning win over Djokovic four years ago even more of a shock.

Ranked 33rd at the time, the Brit was a significant underdog against Djokovic, who was the world No 1 at the time – and who had dispatched a teenage Jannik Sinner in his opener.

However, Evans defied the odds to seal a surprise 6-4, 7-5 triumph over the top seed in the round of 16, and would go on to reach the semi-finals.

It remains the only career meeting between the two.

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2) Alejandro Davidovich Fokina – world No 46 (2022)

One of the most mercurial talents of his generation, Davidovich Fokina pulled off the win of his career against Djokovic in the Monte Carlo second round three years ago.

World No 1 Djokovic was the title favourite and had dropped just a combined seven games against the Spaniard in their two previous matches.

After dropping the opening set, it looked as if the 24-time Grand Slam winner was ready to pounce after forcing a decider – only for the world No 46 to claim a stunning 6-3, 6-7(5), 6-1 triumph.

Davidovich Fokina would go on to reach the final, though this is his only win against Djokovic in six meetings.

1) Jiri Vesely – world No 55 (2016)

One of the strangest statistical anomalies in tennis is that Vesely, a man who has never been ranked inside the top 30, has twice beaten Djokovic without tasting defeat.

The first of those two wins came in Monte Carlo nine years ago, at which time Djokovic was the defending champion – and arguably at the peak of his powers.

No one gave the world No 55 much of a chance, but the Czech pulled off one of the shocks of the 2016 season with a stunning 6-4, 2-6, 6-4 win in their round-two contest.

Vesely, who has a career-high ranking of world No 35, also beat Djokovic at the 2022 Dubai Tennis Championships.