| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-07-31 | Washington | QF | hard | Jack Sock | 7-5 6-4 |
| 2017-02-20 | Delray Beach | F | hard | Jack Sock | W/O |
| 2016-10-10 | Shanghai Masters | R16 | hard | Jack Sock | 0-6 6-4 7-6(8) |
| 2016-06-27 | Wimbledon | R32 | grass | Milos Raonic | 7-6(2) 6-4 7-6(1) |
| 2016-03-21 | Miami Masters | R32 | hard | Milos Raonic | 7-6(3) 6-4 |
| 2014-10-27 | Paris Masters | R32 | hard | Milos Raonic | 6-3 5-7 7-6(4) |
| 2014-08-04 | Canada Masters | R32 | hard | Milos Raonic | 4-6 7-6(2) 7-6(4) |
| 2014-07-28 | Washington | R32 | hard | Milos Raonic | 7-6(3) 7-6(3) |
| 2014-06-23 | Wimbledon | R64 | grass | Milos Raonic | 6-3 6-4 6-4 |
| 2014-03-19 | Miami Masters | R64 | hard | Milos Raonic | 6-4 7-6(1) |
| 2013-02-18 | Memphis | R32 | hard | Jack Sock | 6-3 5-7 7-5 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.