

| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-02-08 | Australian Open | R128 | hard | Grigor Dimitrov | 6-4 6-2 7-6(5) |
| 2019-05-27 | Roland Garros | R64 | clay | Grigor Dimitrov | 6-7(3) 6-4 4-6 7-6(2) 6-3 |
| 2016-08-15 | Cincinnati Masters | SF | hard | Marin Cilic | 4-6 6-3 7-5 |
| 2016-08-08 | Rio Olympics | R64 | hard | Marin Cilic | 6-1 6-4 |
| 2015-11-02 | Paris Masters | R32 | hard | Grigor Dimitrov | 7-6(3) 7-6(2) |
| 2013-12-29 | Brisbane | R16 | hard | Marin Cilic | 7-5 7-5 |
Averages from each player's recent completed matches (19 vs 20). ATP, WTA & Challenger.