Level, 1 wins each over 2 singles meetings since 2022. Last meeting on 02/05/2022 at Mutua Madrid Open - Madrid.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 02/05/2022 | Mutua Madrid Open - Madrid | Round 1 | clay | Dimitrov | 6-2 7-6(4) |
| 08/01/2022 | Melbourne Summer Set - Melbourne | Semi-final | hard | Cressy | 5-7 6-7(9) |
| clay | Dimitrov 1 - 0 Cressy |
| hard | Dimitrov 0 - 1 Cressy |
| 2022 | Dimitrov 1 - 1 Cressy |
161 wins, 103 losses since 2021 (61.0%).
Last matches: D V V V D
121 wins, 121 losses since 2021 (50.0%).
Last matches: D V D V D
Level, 1 wins each over 2 singles meetings since 2022.
On 02/05/2022, at Mutua Madrid Open - Madrid (Round 1): Grigor Dimitrov won 6-2 7-6(4).