
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-04-23 | Madrid Masters | R64 | clay | Stefanos Tsitsipas | 3-6 6-4 6-3 |
| 2024-08-12 | Cincinnati Masters | R64 | hard | Stefanos Tsitsipas | 4-6 6-4 6-3 |
| 2024-06-17 | Halle | R16 | grass | Jan Lennard Struff | 6-4 6-4 |
| 2024-05-06 | Rome Masters | R64 | clay | Stefanos Tsitsipas | 6-7(1) 6-4 6-4 |
| 2023-04-24 | Madrid Masters | QF | clay | Jan Lennard Struff | 7-6(5) 5-7 6-3 |
| 2020-10-26 | Vienna | R32 | hard | Stefanos Tsitsipas | 6-7(3) 6-3 6-4 |
| 2020-02-24 | Dubai | QF | hard | Stefanos Tsitsipas | 4-6 6-4 6-4 |
| 2019-04-22 | Barcelona | R16 | clay | Jan Lennard Struff | 6-4 3-6 6-2 |
| 2019-02-04 | Sofia | R16 | hard | Stefanos Tsitsipas | 7-6(5) 6-4 |
| 2017-09-04 | Genova CH | QF | clay | Stefanos Tsitsipas | 6-2 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.