
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2020-01-20 | Australian Open | SF | hard | Novak Djokovic | 7-6(1) 6-4 6-3 |
| 2019-11-11 | Tour Finals | RR | hard | Roger Federer | 6-4 6-3 |
| 2019-07-01 | Wimbledon | F | grass | Novak Djokovic | 7-6(5) 1-6 7-6(4) 4-6 13-12(3) |
| 2018-10-29 | Paris Masters | SF | hard | Novak Djokovic | 7-6(6) 5-7 7-6(3) |
| 2018-08-13 | Cincinnati Masters | F | hard | Novak Djokovic | 6-4 6-4 |
| 2016-01-18 | Australian Open | SF | hard | Novak Djokovic | 6-1 6-2 3-6 6-3 |
| 2015-11-15 | Tour Finals | RR | hard | Roger Federer | 7-5 6-2 |
| 2015-11-15 | Tour Finals | F | hard | Novak Djokovic | 6-3 6-4 |
| 2015-08-31 | US Open | F | hard | Novak Djokovic | 6-4 5-7 6-4 6-4 |
| 2015-06-29 | Wimbledon | F | grass | Novak Djokovic | 7-6(1) 6-7(10) 6-4 6-3 |
| 2015-05-10 | Rome Masters | F | clay | Novak Djokovic | 6-4 6-3 |
| 2015-03-12 | Indian Wells Masters | F | hard | Novak Djokovic | 6-3 6-7(5) 6-2 |
| 2015-02-23 | Dubai | F | hard | Roger Federer | 6-3 7-5 |
| 2014-11-09 | Tour Finals | F | hard | Novak Djokovic | W/O |
| 2014-10-05 | Shanghai Masters | SF | hard | Roger Federer | 6-4 6-4 |
| 2014-06-23 | Wimbledon | F | grass | Novak Djokovic | 6-7(7) 6-4 7-6(4) 5-7 6-4 |
| 2014-04-13 | Monte Carlo Masters | SF | clay | Roger Federer | 7-5 6-2 |
| 2014-03-06 | Indian Wells Masters | F | hard | Novak Djokovic | 3-6 6-3 7-6(3) |
| 2014-02-24 | Dubai | SF | hard | Roger Federer | 3-6 6-3 6-2 |
| 2013-11-04 | Tour Finals | RR | hard | Novak Djokovic | 6-4 6-7(2) 6-2 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.