Grigor Dimitrov is about to go ahead with his run in the draw in Monte-Carlo. In the previous edition of this tournament, he conquered Ben Shelton 6-1 3-6 6-3.

Draw prediction with head to head records

This is Grigor Dimitrov’s projected draw andhisplausible opposition in Monte-Carlo Rolex Masters. The Bulgarian has a unfavourable record (8-23) against the likely opponents.

R1 – Valentin Vacherot (138) – H2H 0-0
R2 – Miomir Kecmanovic (66) – H2H 1-0
or Matteo Berrettini (84) – H2H 1-1
R3 – Holger Rune (7) – H2H 2-1
or Matteo Arnaldi (38) – H2H 0-0
1/4 – Jannik Sinner (2) – H2H 1-3
or Jan-Lennard Struff (25) – H2H 5-2
1/2 – Daniil Medvedev (4) – H2H 3-7
or Alexander Zverev (5) – H2H 2-7
Fin – Novak Djokovic (1) – H2H 1-12
or Carlos Alcaraz (3) – H2H 2-3
Latest Updated
Draw

R1 – Valentin Vacherot’s rankings and performance.

Head to head record 0-0

34 - 13win/loss in 2025

Rank
140
High
30
Year Total Hard Clay I.hard Grass Carpet
2024 34-13 19-3 15-9 0-0 0-1 0-0
2023 55-32 6-4 49-25 0-3 0-0 0-0
2022 46-22 27-12 18-8 1-2 0-0 0-0
2021 39-14 36-8 2-4 1-2 0-0 0-0
2020 0-1 0-1 0-0 0-0 0-0 0-0
2019 12-6 4-1 8-5 0-0 0-0 0-0
2018 13-6 11-5 0-0 2-1 0-0 0-0
2017 6-9 1-1 3-6 2-2 0-0 0-0

Valentin Vacherot has a 19-4 record in 2024, 1-2 on clay. In the previous 4 years, Valentin has a 70-39 record on clay. The Monegasque won 7 of his last 10 matches.

Valentin’s most significant result of this current season was reaching the final the Nonthaburi 1 Challenger, the Nonthaburi 2 Challenger and the Pune Challenger.

Last year in Monte-Carlo Rolex Masters Valentin lost to Luca Nardi in the 1st round 7-5 7-5.

H2H Grigor Dimitrov vs. Valentin Vacherot

There is no head to head record between Grigor Dimitrov and Valentin Vacherot since this would be the first time that they will face off in the main tour.

R2 – Miomir Kecmanovic’s rankings and performance.

Head to head 1-0 for Grigor Dimitrov

26 - 31win/loss in 2025

Rank
54
High
27
Year Total Hard Clay I.hard Grass Carpet
2024 26-31 10-15 6-7 6-5 4-4 0-0
2023 28-31 11-13 9-9 6-5 2-4 0-0
2022 40-26 21-11 15-8 2-4 2-3 0-0
2021 17-27 6-11 5-8 5-6 1-2 0-0
2020 18-13 7-6 5-2 6-5 0-0 0-0
2019 40-33 24-15 5-6 4-7 7-5 0-0
2018 43-26 27-14 11-9 5-2 0-1 0-0
2017 56-21 9-6 47-15 0-0 0-0 0-0

Miomir Kecmanovic has a 7-10 win-loss record in 2024, 0-2 on clay. During the last 10 years, Kecmanovic has a 111-69 record on clay (Click here to see full career record). The Serbian needs to find his way after he has lost the previous 4 matches.

Last year in Monte-Carlo Rolex Masters Miomir was defeated by Lorenzo Musetti in the 1st round 7-6(1) 6-0.

H2H Grigor Dimitrov vs. Miomir Kecmanovic

This match would represent the 2nd time that Grigor Dimitrov and Miomir Kecmanovic face off. The head to head is 1-0 for Dimitrov (see full H2H stats), but they have never competed against each other on clay in major tournaments.

On the other hand, Grigor Dimitrov may fight against Matteo Berrettini. Their H2H is 1-1

.

R3 – Holger Rune’s rankings and performance.

Head to head 2-1 for Grigor Dimitrov

45 - 24win/loss in 2025

Rank
13
High
4
Year Total Hard Clay I.hard Grass Carpet
2024 45-24 21-12 11-6 10-4 3-2 0-0
2023 44-24 10-10 16-4 11-8 7-2 0-0
2022 50-27 8-9 21-11 21-4 0-3 0-0
2021 73-29 11-5 41-17 21-7 0-0 0-0
2020 32-16 1-3 28-11 3-2 0-0 0-0
2019 6-10 0-3 5-6 1-1 0-0 0-0
2018 1-0 0-0 0-0 1-0 0-0 0-0

Holger Rune has a 13-7 win-loss record in 2024, but he has not played hitherto on clay. Holger won 6 of his last 10 matches.

Rune’s best result of the year was getting to the final Brisbane.

Last year in Monte-Carlo Rolex Masters Rune lost to Andrey Rublev in the final 5-7 6-2 7-5.

H2H Grigor Dimitrov vs. Holger Rune

This would be the 4th time that Grigor Dimitrov and Holger Rune clash against each other. The head to head is 2-1 for Dimitrov (see full H2H stats), but they have never played each other on clay in major tournaments.

Anyhow, Grigor Dimitrov could take on Matteo Arnaldi. Their H2H record is 0-0.

1/4 – Jannik Sinner’s rankings and performance.

Head to head 3-1 for Jannik Sinner

73 - 8win/loss in 2025

Rank
1
High
1
Year Total Hard Clay I.hard Grass Carpet
2024 73-8 40-5 11-2 13-0 9-1 0-0
2023 64-15 28-7 8-3 20-2 8-3 0-0
2022 47-16 21-6 15-4 7-4 4-2 0-0
2021 49-22 22-8 10-6 17-6 0-2 0-0
2020 20-14 2-6 7-3 11-5 0-0 0-0
2019 62-24 12-6 17-8 31-7 2-3 0-0
2018 31-22 13-8 17-12 1-1 0-0 0-1

Jannik Sinner has a 22-1 record in 2024, but he has not played as yet on clay. Sinner will try to keep a positive momentum since he is on a 6 matches winning streak.

His most significant result of this season was conquering the competition at the Australian Open where he defeated Daniil Medvedev in the final 3-6 3-6 6-4 6-4 6-3, in Rotterdam where he beat Alex De Minaur in the final 7-5 6-4, and in Miami where he beat Grigor Dimitrov in the final 6-3 6-1.

Last year in Monte-Carlo Rolex Masters Jannik was defeated by Holger Rune in the semifinal 1-6 7-5 7-5.

H2H Grigor Dimitrov vs. Jannik Sinner

This contest would be 5th time that Grigor Dimitrov and Jannik Sinner clash against each other. The head to head is 3-1 for Sinner (see full H2H stats), but Dimitrov leads 1-0 on clay in major tournaments.

On the other hand, Grigor Dimitrov may come up against Jan-Lennard Struff. Their head to head record is 5-2 for Grigor Dimitrov.

1/2 – Daniil Medvedev’s rankings and performance.

Head to head 7-3 for Daniil Medvedev

46 - 21win/loss in 2025

Rank
5
High
1
Year Total Hard Clay I.hard Grass Carpet
2024 46-21 28-9 11-5 1-5 6-2 0-0
2023 66-18 38-8 10-3 11-4 7-3 0-0
2022 45-19 26-8 3-2 8-6 8-3 0-0
2021 63-13 33-5 5-3 18-3 7-2 0-0
2020 28-10 14-4 0-2 14-4 0-0 0-0
2019 59-21 34-8 8-5 12-5 5-3 0-0
2018 53-25 27-9 1-5 21-7 4-4 0-0
2017 28-28 8-11 0-4 10-9 10-4 0-0

Daniil Medvedev has a 18-4 win-loss record in 2024, but he has not competed as yet on clay. Medvedev won 8 of his last 10 matches.

The Russian’s most significant achievement of the year was reaching the final at the Australian Open and Indian Wells.

Last year in Monte-Carlo Rolex Masters the Russian lost to Holger Rune in the quarter 6-3 6-4.

H2H Grigor Dimitrov vs. Daniil Medvedev

This contest would be 11th time that Grigor Dimitrov and Daniil Medvedev square off. The head to head is 7-3 for Medvedev (see full H2H stats), but they have never competed against each other on clay in major tournaments.

Nonetheless, Grigor Dimitrov may come up against Alexander Zverev. Their H2H is 7-2 for Alexander Zverev.

Final – Novak Djokovic’s rankings and performance.

Head to head 12-1 for Novak Djokovic

37 - 9win/loss in 2025

Rank
7
High
1
Year Total Hard Clay I.hard Grass Carpet
2024 37-9 15-5 16-3 1-0 5-1 0-0
2023 56-7 27-1 12-3 11-2 6-1 0-0
2022 42-7 2-1 14-4 19-2 7-0 0-0
2021 55-7 19-3 18-3 11-1 7-0 0-0
2020 41-5 26-1 11-1 4-3 0-0 0-0
2019 57-11 26-6 15-3 9-2 7-0 0-0
2018 53-13 23-4 11-5 8-3 11-1 0-0
2017 32-8 10-3 12-4 2-0 8-1 0-0

Novak Djokovic has a 8-3 win-loss record in 2024, but he has not played as yet on clay. Djokovic won 7 of his last 10 matches.

The Serbian’s most significant result of the season was getting to the semifinal at the Australian Open .

Last year in Monte-Carlo Rolex Masters the Serbian capitulated to Lorenzo Musetti in the 3rd round 4-6 7-5 6-4.

H2H Grigor Dimitrov vs. Novak Djokovic

This contest would be 14th time that Grigor Dimitrov and Novak Djokovic clash against each other. The head to head is 12-1 for Djokovic (see full H2H stats), 2-1 on clay in major tournaments.

On the other hand, Grigor Dimitrov could play Carlos Alcaraz. Their H2H record is 3-2 for Carlos Alcaraz.