
Milos Raonic defeated Grigor Dimitrov 7-5 3-6 6-3 in the Madrid Masters round of 32 on clay. The upset overturned the form book — Grigor Dimitrov came in leading the head-to-head 3–1, defending last year's round of 16. Milos Raonic narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-01-02 | Brisbane | SF | hard | Grigor Dimitrov | 7-6(7) 6-2 |
| 2014-01-13 | Australian Open | R32 | hard | Grigor Dimitrov | 6-3 3-6 6-4 7-6(10) |
| 2012-12-30 | Brisbane | R16 | hard | Grigor Dimitrov | 6-3 6-4 |
| 2011-10-17 | Stockholm | QF | hard | Milos Raonic | 7-5 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.