| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-08-12 | Cincinnati Masters | R32 | hard | Novak Djokovic | 7-5 6-1 |
| 2016-06-27 | Wimbledon | R32 | grass | Sam Querrey | 7-6(6) 6-1 3-6 7-6(5) |
| 2014-08-25 | US Open | R32 | hard | Novak Djokovic | 6-3 6-2 6-2 |
| 2013-09-30 | Beijing | QF | hard | Novak Djokovic | 6-1 6-2 |
| 2013-04-05 | Davis Cup WG QF: USA vs SRB | RR | hard | Novak Djokovic | 7-5 6-7(4) 6-1 6-0 |
| 2012-10-29 | Paris Masters | R32 | hard | Sam Querrey | 0-6 7-6(5) 6-4 |
| 2012-08-06 | Canada Masters | R16 | hard | Novak Djokovic | 6-4 6-4 |
| 2010-03-05 | Davis Cup WG R1: SRB vs USA | RR | clay | Novak Djokovic | 6-2 7-6(4) 2-6 6-3 |
| 2008-04-20 | Monte Carlo Masters | QF | clay | Novak Djokovic | 6-4 6-0 |
| 2008-01-14 | Australian Open | R32 | hard | Novak Djokovic | 6-3 6-1 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.