| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2018-08-27 | US Open | R32 | hard | Novak Djokovic | 6-2 6-3 6-3 |
| 2015-06-29 | Wimbledon | SF | grass | Novak Djokovic | 7-6(2) 6-4 6-4 |
| 2015-05-24 | Roland Garros | R16 | clay | Novak Djokovic | 6-1 6-2 6-3 |
| 2013-11-04 | Tour Finals | RR | hard | Novak Djokovic | 7-6(5) 4-6 6-3 |
| 2013-09-30 | Beijing | SF | hard | Novak Djokovic | 6-4 6-2 |
| 2013-08-05 | Canada Masters | QF | hard | Novak Djokovic | 6-1 6-2 |
| 2012-08-06 | Canada Masters | F | hard | Novak Djokovic | 6-3 6-2 |
| 2011-05-22 | Roland Garros | R16 | clay | Novak Djokovic | 6-4 6-4 6-2 |
| 2011-03-10 | Indian Wells Masters | QF | hard | Novak Djokovic | 6-2 6-4 |
| 2010-10-10 | Shanghai Masters | R16 | hard | Novak Djokovic | 6-1 6-1 |
| 2007-11-12 | Masters Cup | RR | hard | Richard Gasquet | 6-4 6-2 |
| 2007-04-29 | Estoril | F | clay | Novak Djokovic | 7-6(7) 0-6 6-1 |
| 2006-10-16 | Madrid Masters | R32 | clay | Novak Djokovic | 7-6(2) 1-6 6-1 |
Averages from each player's recent completed matches (20 vs 19). ATP, WTA & Challenger.