| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-08-02 | Washington | R64 | hard | Kei Nishikori | 6-4 6-3 |
| 2018-10-08 | Shanghai Masters | R16 | hard | Kei Nishikori | 7-6(7) 6-4 |
| 2016-02-22 | Acapulco | R16 | hard | Sam Querrey | 6-4 6-3 |
| 2016-02-08 | Memphis | SF | hard | Kei Nishikori | 3-6 6-3 6-3 |
| 2015-10-05 | Tokyo | R16 | hard | Kei Nishikori | 7-6(3) 6-3 |
| 2015-02-09 | Memphis | SF | hard | Kei Nishikori | 5-7 7-6(5) 7-6(5) |
| 2012-10-07 | Shanghai Masters | R32 | hard | Sam Querrey | 2-6 6-1 6-4 |
| 2012-08-06 | Canada Masters | R32 | hard | Sam Querrey | 6-2 6-3 |
| 2011-06-06 | Queen's Club | R64 | grass | Sam Querrey | 6-3 6-4 |
| 2008-02-11 | Delray Beach | SF | hard | Kei Nishikori | 4-6 6-2 7-6(7) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.