| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2020-08-24 | Cincinnati Masters | R16 | hard | Milos Raonic | 6-2 6-2 |
| 2016-11-14 | Tour Finals | SF | hard | Andy Murray | 5-7 7-6(5) 7-6(9) |
| 2016-10-31 | Paris Masters | SF | hard | Andy Murray | W/O |
| 2016-08-15 | Cincinnati Masters | SF | hard | Andy Murray | 6-3 6-3 |
| 2016-06-27 | Wimbledon | F | grass | Andy Murray | 6-4 7-6(3) 7-6(2) |
| 2016-06-13 | Queen's Club | F | grass | Andy Murray | 6-7(5) 6-4 6-3 |
| 2016-04-11 | Monte Carlo Masters | QF | clay | Andy Murray | 6-2 6-0 |
| 2016-01-18 | Australian Open | SF | hard | Andy Murray | 4-6 7-5 6-7(4) 6-4 6-2 |
| 2015-05-03 | Madrid Masters | QF | clay | Andy Murray | 6-4 7-5 |
| 2014-11-09 | Tour Finals | RR | hard | Andy Murray | 6-3 7-5 |
| 2012-10-01 | Tokyo | SF | hard | Milos Raonic | 6-3 6-7(5) 7-6(4) |
| 2012-08-27 | US Open | R16 | hard | Andy Murray | 6-4 6-4 6-2 |
| 2012-08-06 | Canada Masters | R16 | hard | Milos Raonic | W/O |
| 2012-04-23 | Barcelona | QF | clay | Milos Raonic | 6-4 7-6(3) |
| 2012-03-21 | Miami Masters | R32 | hard | Andy Murray | W/O |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.