| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-02-11 | Rotterdam | SF | hard | Stan Wawrinka | 6-2 4-6 6-4 |
| 2018-08-13 | Cincinnati Masters | R32 | hard | Stan Wawrinka | 6-4 6-4 |
| 2017-01-02 | Brisbane | SF | hard | Kei Nishikori | 7-6(3) 6-3 |
| 2016-11-14 | Tour Finals | RR | hard | Kei Nishikori | 6-2 6-3 |
| 2016-08-29 | US Open | SF | hard | Stan Wawrinka | 4-6 7-5 6-4 6-2 |
| 2016-07-25 | Canada Masters | SF | hard | Kei Nishikori | 7-6(6) 6-1 |
| 2015-01-19 | Australian Open | QF | hard | Stan Wawrinka | 6-3 6-4 7-6(6) |
| 2014-08-25 | US Open | QF | hard | Kei Nishikori | 3-6 7-5 7-6(7) 6-7(5) 6-4 |
| 2012-08-12 | Cincinnati Masters | R16 | hard | Stan Wawrinka | 6-3 6-3 |
| 2012-02-20 | Buenos Aires | QF | clay | Stan Wawrinka | 6-4 6-2 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.