| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-01-02 | Doha | QF | hard | Novak Djokovic | 6-3 6-3 |
| 2016-07-25 | Canada Masters | R16 | hard | Novak Djokovic | 6-2 6-4 |
| 2014-06-23 | Wimbledon | R64 | grass | Novak Djokovic | 6-4 6-3 6-7(5) 7-6(5) |
| 2014-05-11 | Rome Masters | R32 | clay | Novak Djokovic | 6-3 7-5 |
| 2013-11-15 | Davis Cup WG F: SRB vs CZE | RR | hard | Novak Djokovic | 7-5 6-1 6-4 |
| 2013-01-14 | Australian Open | R32 | hard | Novak Djokovic | 6-4 6-3 7-5 |
| 2012-06-25 | Wimbledon | R32 | grass | Novak Djokovic | 4-6 6-2 6-2 6-2 |
| 2011-08-14 | Cincinnati Masters | R16 | hard | Novak Djokovic | 6-3 6-3 |
| 2009-08-31 | US Open | R16 | hard | Novak Djokovic | 6-1 6-3 6-3 |
| 2008-05-05 | Rome Masters | SF | clay | Novak Djokovic | 6-0 1-0 RET |
| 2007-08-27 | US Open | R64 | hard | Novak Djokovic | 6-7(4) 7-6(5) 5-7 7-5 7-6(2) |
| 2006-02-20 | Rotterdam | QF | hard | Radek Stepanek | 7-5 4-6 7-6(2) |
| 2006-01-30 | Zagreb | R16 | hard | Novak Djokovic | 6-3 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.