| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-05-27 | Roland Garros | R128 | clay | Grigor Dimitrov | 6-3 6-0 3-6 6-7(4) 6-4 |
| 2019-01-14 | Australian Open | R128 | hard | Grigor Dimitrov | 4-6 6-3 6-1 6-4 |
| 2016-06-13 | Queen's Club | R32 | grass | Janko Tipsarevic | 7-6(6) 4-6 6-3 |
| 2013-04-14 | Monte Carlo Masters | R32 | clay | Grigor Dimitrov | 7-6(3) 6-1 |
| 2012-03-21 | Miami Masters | R16 | hard | Janko Tipsarevic | 7-6(3) 6-2 |
| 2011-06-12 | Eastbourne | QF | grass | Janko Tipsarevic | 6-3 7-6(2) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.