| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-02-08 | Australian Open | R16 | hard | Novak Djokovic | 7-6(4) 4-6 6-1 6-4 |
| 2020-08-24 | Cincinnati Masters | F | hard | Novak Djokovic | 1-6 6-3 6-4 |
| 2020-01-20 | Australian Open | QF | hard | Novak Djokovic | 6-4 6-3 7-6(1) |
| 2018-08-13 | Cincinnati Masters | QF | hard | Novak Djokovic | 7-5 4-6 6-3 |
| 2016-11-14 | Tour Finals | RR | hard | Novak Djokovic | 7-6(6) 7-6(5) |
| 2016-05-02 | Madrid Masters | QF | clay | Novak Djokovic | 6-3 6-4 |
| 2016-03-07 | Indian Wells Masters | F | hard | Novak Djokovic | 6-2 6-0 |
| 2015-01-19 | Australian Open | QF | hard | Novak Djokovic | 7-6(5) 6-4 6-2 |
| 2014-10-27 | Paris Masters | F | hard | Novak Djokovic | 6-2 6-3 |
| 2014-05-26 | Roland Garros | QF | clay | Novak Djokovic | 7-5 7-6(5) 6-4 |
| 2014-05-11 | Rome Masters | SF | clay | Novak Djokovic | 6-7(5) 7-6(4) 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.