| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-08-25 | US Open | R16 | hard | Novak Djokovic | 6-3 6-3 6-2 |
| 2021-11-27 | Davis Cup Finals RR: SRB vs GER | RR | hard | Novak Djokovic | 6-2 6-4 |
| 2021-07-24 | Tokyo Olympics | R32 | hard | Novak Djokovic | 6-4 6-3 |
| 2020-08-24 | Cincinnati Masters | QF | hard | Novak Djokovic | 6-3 6-1 |
| 2020-01-20 | Australian Open | R128 | hard | Novak Djokovic | 7-6(5) 6-2 2-6 6-1 |
| 2019-05-27 | Roland Garros | R16 | clay | Novak Djokovic | 6-3 6-2 6-2 |
| 2017-01-02 | Doha | R32 | hard | Novak Djokovic | 7-6(1) 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.