| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-07-21 | Washington | R32 | hard | Daniil Medvedev | 3-6 7-5 6-1 |
| 2025-06-09 | s Hertogenbosch | QF | grass | Reilly Opelka | 7-6(5) 7-6(5) |
| 2021-08-09 | Canada Masters | F | hard | Daniil Medvedev | 6-4 6-3 |
| 2021-05-31 | Roland Garros | R32 | clay | Daniil Medvedev | 6-4 6-2 6-4 |
| 2020-10-12 | St Petersburg | R16 | hard | Reilly Opelka | 2-6 7-5 6-4 |
| 2019-03-18 | Miami Masters | R32 | hard | Daniil Medvedev | 7-6(5) 6-7(5) 7-6(0) |
Averages from each player's recent completed matches (19 vs 19). ATP, WTA & Challenger.