
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-01-14 | Australian Open | R32 | hard | Marin Cilic | 4-6 3-6 6-1 7-6(8) 6-3 |
| 2018-04-16 | Monte Carlo Masters | R32 | clay | Marin Cilic | 6-3 7-6(4) |
| 2016-10-03 | Tokyo | R16 | hard | Marin Cilic | 4-6 7-5 7-5 |
| 2016-08-15 | Cincinnati Masters | R32 | hard | Marin Cilic | 6-3 6-1 |
| 2015-05-03 | Madrid Masters | R32 | clay | Fernando Verdasco | 6-7(5) 7-6(5) 6-3 |
| 2014-08-10 | Cincinnati Masters | R32 | hard | Marin Cilic | 7-6(6) 7-6(5) |
| 2012-10-21 | Valencia | R16 | hard | Marin Cilic | 6-1 6-4 |
| 2012-10-07 | Shanghai Masters | R16 | hard | Marin Cilic | 4-6 6-1 6-4 |
| 2011-11-07 | Paris Masters | R64 | hard | Fernando Verdasco | 3-6 6-2 6-3 |
| 2010-03-24 | Miami Masters | R16 | hard | Fernando Verdasco | 6-4 7-6(3) |
| 2009-11-08 | Paris Masters | R16 | hard | Marin Cilic | 3-6 6-3 6-4 |
| 2008-10-12 | Madrid Masters | R32 | clay | Marin Cilic | 6-2 6-3 |
| 2008-06-16 | Nottingham | SF | grass | Fernando Verdasco | 6-3 6-1 |
| 2007-10-22 | St. Petersburg | SF | carpet | Fernando Verdasco | 6-2 6-3 |
Averages from each player's recent completed matches (19 vs 20). ATP, WTA & Challenger.