| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-02-22 | Dubai | R32 | hard | Novak Djokovic | 6-1 6-2 |
| 2014-08-10 | Cincinnati Masters | R16 | hard | Tommy Robredo | 7-6(6) 7-5 |
| 2014-03-19 | Miami Masters | R16 | hard | Novak Djokovic | 6-3 7-5 |
| 2008-08-25 | US Open | R16 | hard | Novak Djokovic | 4-6 6-2 6-3 5-7 6-3 |
| 2007-04-29 | Estoril | SF | clay | Novak Djokovic | 7-5 6-1 |
| 2007-02-19 | Rotterdam | QF | hard | Novak Djokovic | 4-6 6-4 7-5 |
| 2006-06-26 | Wimbledon | R64 | grass | Novak Djokovic | 7-6(5) 6-2 6-4 |
| 2005-10-31 | Paris Masters | R16 | hard | Tommy Robredo | 6-4 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.