Novak Djokovic’s 5 worst Monte Carlo Masters defeats

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.