Grigor Dimitrov leads 2 to 1 over 3 singles meetings since 2022. Last meeting on 25/03/2025 at Miami Open - Miami.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 25/03/2025 | Miami Open - Miami | Round 4 | hard | Dimitrov | 6-4 7-5 |
| 31/08/2022 | U.S. Open - New York | Round 2 | hard | Nakashima | 6-7(5) 5-7 3-6 |
| 10/05/2022 | Internazionali BNL d'Italia - Rome | Round 1 | clay | Dimitrov | 6-3 6-4 |
| hard | Dimitrov 1 - 1 Nakashima |
| clay | Dimitrov 1 - 0 Nakashima |
| 2025 | Dimitrov 1 - 0 Nakashima |
| 2022 | Dimitrov 1 - 1 Nakashima |
161 wins, 103 losses since 2021 (61.0%).
Last matches: D V V V D
221 wins, 151 losses since 2021 (59.4%).
Last matches: D V D V V
Grigor Dimitrov leads 2 to 1 over 3 singles meetings since 2022.
On 25/03/2025, at Miami Open - Miami (Round 4): Grigor Dimitrov won 6-4 7-5.