Alejandro Tabilo beats Novak Djokovic again

For the second time in his tennis career in two meetings, Alejandro Tabilo of Chile has defeated Novak Djokovic, the 24-time grand slam champion. In the second round of the 2025 Monte Carlo Masters on Wednesday, Tabilo came through with a convincing 6-3, 6-4 win. Tabilo previously beat Djokovic 6-2, 6-3 in the third round of the 2024 Italian Open.

On Wednesday, Tabilo broke Djokovic three times in eight opportunities. Tabilo won 81% of the points on his first serve and 55% of the points on his second serve. Djokovic won 67% of the points on his first serve and 46% of the points on his second serve.

Djokovic is the second grand slam champion Tabilo beat in Monte Carlo this week. On Monday, Tabilo defeated three-time grand slam champion Stanislas Wawrinka of Switzerland 1-6, 7-5, 7-5.  In Tabilo’s first two matches in Monte Carlo this week, he was the betting underdog.

Tabilo faced Grigor Dimitrov of Bulgaria in the third round on Thursday, and lost 6-3, 3-6, 6-2. Dimitriov will now face Australia’s Alex de Minaur in the quarterfinals on Friday. De Minaur is coming off an impressive 6-2, 6-2 win over 2021 United States Open champion Daniil Medvedev of Russia,

Head-to-head between de Minaur and Dimitrov, de Minaur has won three of five matches. Their last meeting was in the semifinals of Rotterdam in 2024, which de Minaur won 6-4, 6-3.

For de Minaur, this is the fifth time he has reached at least the quarterfinals of a Tennis Masters 1000 series event. He reached the quarterfinals of the 2023 and 2024 Paris Masters,  the 2024 Monte Carlo Masters and the finals of the 2023 Canadian Open.

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