Milos Raonic defeated Gilles Simon 6-3 6-4 6-4 in the US Open round of 64 on hard. The result followed the form book — Milos Raonic came in leading the head-to-head 4–1. Milos Raonic extended the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-01-16 | Australian Open | R32 | hard | Milos Raonic | 6-2 7-6(5) 3-6 6-3 |
| 2015-06-15 | Queen's Club | QF | grass | Gilles Simon | 4-6 6-3 7-5 |
| 2014-09-29 | Tokyo | SF | hard | Milos Raonic | 6-1 6-4 |
| 2014-05-26 | Roland Garros | R32 | clay | Milos Raonic | 4-6 6-3 2-6 6-2 7-5 |
| 2011-04-25 | Estoril | QF | clay | Milos Raonic | 7-6(4) 4-6 6-3 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (144 vs 200). ATP, WTA & Challenger.