| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-05-08 | Rome Masters | R64 | clay | Grigor Dimitrov | 6-4 7-6(3) |
| 2020-02-24 | Acapulco | QF | hard | Grigor Dimitrov | 6-4 6-4 |
| 2019-08-12 | Cincinnati Masters | R64 | hard | Stan Wawrinka | 5-7 6-4 7-6(4) |
| 2019-05-27 | Roland Garros | R32 | clay | Stan Wawrinka | 7-6(5) 7-6(4) 7-6(8) |
| 2018-08-27 | US Open | R128 | hard | Stan Wawrinka | 6-3 6-2 7-5 |
| 2018-07-02 | Wimbledon | R128 | grass | Stan Wawrinka | 1-6 7-6(3) 7-6(5) 6-4 |
| 2016-08-15 | Cincinnati Masters | R16 | hard | Grigor Dimitrov | 6-4 6-4 |
| 2015-05-03 | Madrid Masters | R16 | clay | Grigor Dimitrov | 7-6(5) 3-6 6-3 |
| 2015-04-12 | Monte Carlo Masters | R16 | clay | Grigor Dimitrov | 6-1 6-2 |
| 2014-06-09 | Queen's Club | SF | grass | Grigor Dimitrov | 6-2 6-4 |
| 2013-05-05 | Madrid Masters | R16 | clay | Stan Wawrinka | 3-6 6-4 6-1 |
| 2011-01-17 | Australian Open | R64 | hard | Stan Wawrinka | 7-5 6-3 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.