Jannik Sinner leads 5 to 0 over 5 singles meetings since 2023. Last meeting on 06/07/2025 at Wimbledon - London.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 06/07/2025 | Wimbledon - London | Round 4 | grass | Sinner | 3-6 5-7 2-2 |
| 04/06/2024 | French Open - Paris | Quarter-final | clay | Sinner | 2-6 4-6 6-7(3) |
| 31/03/2024 | Miami Open - Miami | Final | hard | Sinner | |
| 02/10/2023 | China Open - Beijing | Quarter-final | hard | Sinner | 4-6 6-3 2-6 |
| 26/03/2023 | Miami Open - Miami | Round 3 | hard | Sinner | 6-3 6-4 |
| grass | Dimitrov 0 - 1 Sinner |
| clay | Dimitrov 0 - 1 Sinner |
| hard | Dimitrov 0 - 3 Sinner |
| 2025 | Dimitrov 0 - 1 Sinner |
| 2024 | Dimitrov 0 - 2 Sinner |
| 2023 | Dimitrov 0 - 2 Sinner |
161 wins, 103 losses since 2021 (61.0%).
Last matches: D V V V D
324 wins, 75 losses since 2021 (81.2%).
Last matches: V V V V V
Jannik Sinner leads 5 to 0 over 5 singles meetings since 2023.
On 06/07/2025, at Wimbledon - London (Round 4): Jannik Sinner won 3-6 5-7 2-2.