

| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-07-03 | Wimbledon | R32 | grass | Novak Djokovic | 6-3 6-1 7-6(5) |
| 2022-05-09 | Rome Masters | R16 | clay | Novak Djokovic | 6-2 6-2 |
| 2016-08-29 | US Open | F | hard | Stan Wawrinka | 6-7(1) 6-4 7-5 6-3 |
| 2015-11-02 | Paris Masters | SF | hard | Novak Djokovic | 6-3 3-6 6-0 |
| 2015-08-16 | Cincinnati Masters | QF | hard | Novak Djokovic | 6-4 6-1 |
| 2015-05-24 | Roland Garros | F | clay | Stan Wawrinka | 4-6 6-4 6-3 6-4 |
| 2015-01-19 | Australian Open | SF | hard | Novak Djokovic | 7-6(1) 3-6 6-4 4-6 6-0 |
| 2014-11-09 | Tour Finals | RR | hard | Novak Djokovic | 6-3 6-0 |
| 2014-01-13 | Australian Open | QF | hard | Stan Wawrinka | 2-6 6-4 6-2 3-6 9-7 |
| 2013-11-04 | Tour Finals | SF | hard | Novak Djokovic | 6-3 6-3 |
| 2013-10-28 | Paris Masters | QF | hard | Novak Djokovic | 6-1 6-4 |
| 2013-08-26 | US Open | SF | hard | Novak Djokovic | 2-6 7-6(4) 3-6 6-3 6-4 |
| 2013-01-14 | Australian Open | R16 | hard | Novak Djokovic | 1-6 7-5 6-4 6-7(5) 12-10 |
| 2012-08-27 | US Open | R16 | hard | Novak Djokovic | 6-4 6-1 3-1 RET |
| 2012-05-06 | Madrid Masters | R16 | clay | Novak Djokovic | 7-6(5) 6-4 |
| 2011-05-08 | Rome Masters | R16 | clay | Novak Djokovic | 6-4 6-1 |
| 2010-04-11 | Monte Carlo Masters | R16 | clay | Novak Djokovic | 6-4 6-4 |
| 2009-11-02 | Basel | QF | hard | Novak Djokovic | 3-6 7-6(5) 6-2 |
| 2009-04-12 | Monte Carlo Masters | SF | clay | Novak Djokovic | 4-6 6-1 6-3 |
| 2009-03-12 | Indian Wells Masters | R16 | hard | Novak Djokovic | 7-6(7) 7-6(6) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.