

| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2026-02-16 | Doha | QF | hard | Andrey Rublev | 6-3 7-6(2) |
| 2022-11-14 | Tour Finals | RR | hard | Andrey Rublev | 3-6 6-3 6-2 |
| 2022-10-03 | Astana | SF | hard | Stefanos Tsitsipas | 4-6 6-4 6-3 |
| 2022-05-02 | Madrid Masters | QF | clay | Stefanos Tsitsipas | 6-3 2-6 6-4 |
| 2021-11-15 | Tour Finals | RR | hard | Andrey Rublev | 6-4 6-4 |
| 2021-04-12 | Monte Carlo Masters | F | clay | Stefanos Tsitsipas | 6-3 6-3 |
| 2021-03-01 | Rotterdam | SF | hard | Andrey Rublev | 6-3 7-6(2) |
| 2020-11-16 | Tour Finals | RR | hard | Stefanos Tsitsipas | 6-1 4-6 7-6(6) |
| 2020-09-28 | Roland Garros | QF | clay | Stefanos Tsitsipas | 7-5 6-2 6-3 |
| 2019-08-26 | US Open | R128 | hard | Andrey Rublev | 6-4 6-7(5) 7-6(7) 7-5 |
| 2018-11-05 | NextGen Finals | SF | hard | Stefanos Tsitsipas | 4-3(3) 3-4(5) 4-0 2-4 4-3(2) |
| 2017-01-30 | Quimper CH | R32 | hard | Andrey Rublev | 6-2 3-6 7-6(7) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.