Daniil Medvedev leads 7 to 2 over 9 singles meetings since 2021. Last meeting on 29/10/2025 at Rolex Paris Masters - Paris.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 29/10/2025 | Rolex Paris Masters - Paris | Round 2 | indoor hard | Medvedev | |
| 07/07/2024 | Wimbledon - London | Round 4 | grass | Medvedev | 3-5 |
| 13/03/2024 | BNP Paribas Open - Indian Wells | Round 4 | hard | Medvedev | 6-4 5-4 |
| 01/11/2023 | Rolex Paris Masters - Paris | Round 2 | indoor hard | Dimitrov | 6-3 6-7(4) 7-6(2) |
| 26/10/2023 | Erste Bank Open - Vienna | Round 2 | indoor hard | Medvedev | 3-6 6-2 6-4 |
| 18/02/2023 | ABN AMRO World Tennis Tournament - Rotterdam | Semi-final | indoor hard | Medvedev | 6-1 6-2 |
| 29/10/2022 | Erste Bank Open - Vienna | Semi-final | indoor hard | Medvedev | 6-4 6-2 |
| 13/10/2021 | BNP Paribas Open - Indian Wells | Round 4 | hard | Dimitrov | 6-4 4-6 3-6 |
| 19/08/2021 | Western & Southern Open - Cincinnati | Round 3 | hard | Medvedev | 6-3 6-3 |
| indoor hard | Dimitrov 1 - 4 Medvedev |
| grass | Dimitrov 0 - 1 Medvedev |
| hard | Dimitrov 1 - 2 Medvedev |
| 2025 | Dimitrov 0 - 1 Medvedev |
| 2024 | Dimitrov 0 - 2 Medvedev |
| 2023 | Dimitrov 1 - 2 Medvedev |
| 2022 | Dimitrov 0 - 1 Medvedev |
| 2021 | Dimitrov 1 - 1 Medvedev |
161 wins, 103 losses since 2021 (61.0%).
Last matches: D V V V D
294 wins, 108 losses since 2021 (73.1%).
Last matches: V V V D D
Daniil Medvedev leads 7 to 2 over 9 singles meetings since 2021.
On 29/10/2025, at Rolex Paris Masters - Paris (Round 2): Daniil Medvedev won.