
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2020-11-16 | Tour Finals | SF | hard | Dominic Thiem | 7-5 6-7(10) 7-6(5) |
| 2020-01-20 | Australian Open | F | hard | Novak Djokovic | 6-4 4-6 2-6 6-3 6-4 |
| 2019-11-11 | Tour Finals | RR | hard | Dominic Thiem | 6-7(5) 6-3 7-6(5) |
| 2019-05-27 | Roland Garros | SF | clay | Dominic Thiem | 6-2 3-6 7-5 5-7 7-5 |
| 2019-05-06 | Madrid Masters | SF | clay | Novak Djokovic | 7-6(2) 7-6(4) |
| 2018-04-16 | Monte Carlo Masters | R16 | clay | Dominic Thiem | 6-7(2) 6-2 6-3 |
| 2017-05-29 | Roland Garros | QF | clay | Dominic Thiem | 7-6(5) 6-3 6-0 |
| 2017-05-15 | Rome Masters | SF | clay | Novak Djokovic | 6-1 6-0 |
| 2016-11-14 | Tour Finals | RR | hard | Novak Djokovic | 6-7(10) 6-0 6-2 |
| 2016-03-21 | Miami Masters | R16 | hard | Novak Djokovic | 6-3 6-4 |
| 2014-10-05 | Shanghai Masters | R32 | hard | Novak Djokovic | 6-3 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.