| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2022-05-09 | Rome Masters | R16 | clay | Denis Shapovalov | 1-6 7-5 6-2 |
| 2022-01-17 | Australian Open | QF | hard | Rafael Nadal | 6-3 6-4 4-6 3-6 6-3 |
| 2021-05-10 | Rome Masters | R16 | clay | Rafael Nadal | 3-6 6-4 7-6(3) |
| 2019-11-24 | Davis Cup Finals F: CAN vs ESP | RR | hard | Rafael Nadal | 6-3 7-6(7) |
| 2019-10-28 | Paris Masters | SF | hard | Denis Shapovalov | W/O |
| 2018-05-14 | Rome Masters | R16 | clay | Rafael Nadal | 6-4 6-1 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.