| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2024-04-15 | Barcelona | SF | clay | Stefanos Tsitsipas | 5-7 6-4 6-2 |
| 2020-09-21 | Hamburg | QF | clay | Stefanos Tsitsipas | 7-6(5) 6-2 |
| 2019-09-30 | Beijing | R32 | hard | Stefanos Tsitsipas | 4-6 6-3 6-4 |
| 2018-05-14 | Rome Masters | Q2 | clay | Stefanos Tsitsipas | 7-6(9) 6-4 |
| 2018-04-16 | Monte Carlo Masters | Q3 | clay | Dusan Lajovic | – |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.