
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-08-30 | US Open | R32 | hard | Novak Djokovic | 6-7(4) 6-3 6-3 6-2 |
| 2021-07-24 | Tokyo Olympics | QF | hard | Novak Djokovic | 6-2 6-0 |
| 2019-01-14 | Australian Open | QF | hard | Novak Djokovic | 6-1 4-1 RET |
| 2018-08-27 | US Open | SF | hard | Novak Djokovic | 6-3 6-4 6-2 |
| 2018-07-02 | Wimbledon | QF | grass | Novak Djokovic | 6-3 3-6 6-2 6-2 |
| 2018-05-14 | Rome Masters | QF | clay | Novak Djokovic | 2-6 6-1 6-3 |
| 2018-05-07 | Madrid Masters | R64 | clay | Novak Djokovic | 7-5 6-4 |
| 2017-05-08 | Madrid Masters | QF | clay | Novak Djokovic | W/O |
| 2016-11-14 | Tour Finals | SF | hard | Novak Djokovic | 6-1 6-1 |
| 2016-07-25 | Canada Masters | F | hard | Novak Djokovic | 6-3 7-5 |
| 2016-05-09 | Rome Masters | SF | clay | Novak Djokovic | 2-6 6-4 7-6(5) |
| 2016-05-02 | Madrid Masters | SF | clay | Novak Djokovic | 6-3 7-6(4) |
| 2016-03-21 | Miami Masters | F | hard | Novak Djokovic | 6-3 6-3 |
| 2016-01-18 | Australian Open | QF | hard | Novak Djokovic | 6-3 6-2 6-4 |
| 2015-11-15 | Tour Finals | RR | hard | Novak Djokovic | 6-1 6-1 |
| 2015-05-10 | Rome Masters | QF | clay | Novak Djokovic | 6-3 3-6 6-1 |
| 2014-11-09 | Tour Finals | SF | hard | Novak Djokovic | 6-1 3-6 6-0 |
| 2014-10-27 | Paris Masters | SF | hard | Novak Djokovic | 6-2 6-3 |
| 2014-03-19 | Miami Masters | SF | hard | Novak Djokovic | W/O |
| 2011-10-31 | Basel | SF | hard | Kei Nishikori | 2-6 7-6(4) 6-0 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.