| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-01-14 | Australian Open | R128 | hard | Milos Raonic | 6-4 7-6(5) 6-4 |
| 2016-06-13 | Queen's Club | R32 | grass | Milos Raonic | 6-7(5) 6-4 6-4 |
| 2016-05-09 | Rome Masters | R32 | clay | Nick Kyrgios | 7-6(5) 6-3 |
| 2016-03-21 | Miami Masters | QF | hard | Nick Kyrgios | 6-4 7-6(4) |
| 2015-06-29 | Wimbledon | R32 | grass | Nick Kyrgios | 5-7 7-5 7-6(3) 6-3 |
| 2014-06-23 | Wimbledon | QF | grass | Milos Raonic | 6-7(4) 6-2 6-4 7-6(4) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.