Head to head
3
Hard
0
2
Clay
0
0
Grass
1
Milos Raonic's wins on the left · Gilles Simon's on the right · bar lengths share one scale
Momentum
Running lead across all meetings, oldest to newest (walkovers excluded).
All meetings (6)
| 2018 | US Open | Hard | R64 | Milos Raonic | 6-3 6-4 6-4 |
| 2017 | Australian Open | Hard | R32 | Milos Raonic | 6-2 7-6(5) 3-6 6-3 |
| 2015 | Queen's Club | Grass | QF | Gilles Simon | 4-6 6-3 7-5 |
| 2014 | Tokyo | Hard | SF | Milos Raonic | 6-1 6-4 |
| 2014 | Roland Garros | Clay | R32 | Milos Raonic | 4-6 6-3 2-6 6-2 7-5 |
| 2011 | Estoril | Clay | QF | Milos Raonic | 7-6(4) 4-6 6-3 |
Methodology
Head-to-head totals and surface splits exclude walkovers (no match was played), which follows ATP convention — walkover meetings still appear in the match list. The momentum chart plots the running lead across all counted meetings, oldest to newest.