| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-04-17 | Monte Carlo Masters | R32 | clay | Novak Djokovic | 6-3 3-6 7-5 |
| 2016-01-18 | Australian Open | R16 | hard | Novak Djokovic | 6-3 6-7(1) 6-4 4-6 6-3 |
| 2015-11-02 | Paris Masters | R16 | hard | Novak Djokovic | 6-3 7-5 |
| 2014-08-10 | Cincinnati Masters | R32 | hard | Novak Djokovic | 6-3 4-6 6-4 |
| 2014-06-23 | Wimbledon | R32 | grass | Novak Djokovic | 6-4 6-2 6-4 |
| 2010-12-03 | Davis Cup WG F: SRB vs FRA | RR | hard | Novak Djokovic | 6-3 6-1 7-5 |
| 2010-10-04 | Beijing | QF | hard | Novak Djokovic | 6-3 6-2 |
| 2009-08-16 | Cincinnati Masters | QF | hard | Novak Djokovic | 6-4 7-5 |
| 2009-02-23 | Dubai | SF | hard | Novak Djokovic | 3-6 7-5 7-5 |
| 2008-11-09 | Masters Cup | SF | hard | Novak Djokovic | 4-6 6-3 7-5 |
| 2008-02-11 | Marseille | R16 | hard | Gilles Simon | 6-2 6-7(6) 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.