
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-05-06 | Madrid Masters | R16 | clay | Novak Djokovic | 6-1 7-6(2) |
| 2018-10-08 | Shanghai Masters | R32 | hard | Novak Djokovic | 6-3 7-5 |
| 2018-06-18 | Queen's Club | SF | grass | Novak Djokovic | 7-6(5) 6-4 |
| 2015-08-10 | Canada Masters | SF | hard | Novak Djokovic | 6-4 6-4 |
| 2014-05-26 | Roland Garros | R64 | clay | Novak Djokovic | 6-1 6-4 6-2 |
| 2014-03-19 | Miami Masters | R64 | hard | Novak Djokovic | 6-4 6-3 |
| 2013-06-24 | Wimbledon | R32 | grass | Novak Djokovic | 6-3 6-2 6-2 |
| 2011-06-20 | Wimbledon | R128 | grass | Novak Djokovic | 6-4 6-1 6-1 |
| 2010-08-09 | Canada Masters | QF | hard | Novak Djokovic | 6-2 6-3 |
| 2010-04-25 | Rome Masters | R32 | clay | Novak Djokovic | 6-1 6-1 |
| 2009-08-16 | Cincinnati Masters | R16 | hard | Novak Djokovic | 7-5 6-3 |
| 2009-02-16 | Marseille | R32 | hard | Novak Djokovic | 7-6(4) 6-4 |
| 2009-01-19 | Australian Open | R64 | hard | Novak Djokovic | 7-5 6-1 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.