Grigor Dimitrov leads 2 to 1 over 3 singles meetings since 2021. Last meeting on 23/03/2025 at Miami Open - Miami.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 23/03/2025 | Miami Open - Miami | Round 3 | hard | Dimitrov | 6-7(3) 6-4 7-5 |
| 01/11/2024 | Rolex Paris Masters - Paris | Quarter-final | indoor hard | Khachanov | 6-2 6-3 |
| 03/11/2021 | Rolex Paris Masters - Paris | Round 2 | indoor hard | Dimitrov | 4-6 6-2 6-0 |
| hard | Dimitrov 1 - 0 Khachanov |
| indoor hard | Dimitrov 1 - 1 Khachanov |
| 2025 | Dimitrov 1 - 0 Khachanov |
| 2024 | Dimitrov 0 - 1 Khachanov |
| 2021 | Dimitrov 1 - 0 Khachanov |
162 wins, 107 losses since 2021 (60.2%).
Last matches: D D D D V
187 wins, 130 losses since 2021 (59.0%).
Last matches: D V D D V
Grigor Dimitrov leads 2 to 1 over 3 singles meetings since 2021.
On 23/03/2025, at Miami Open - Miami (Round 3): Grigor Dimitrov won 6-7(3) 6-4 7-5.