01/By surface
each with its own count, at equal weight
Hard
3-0
M. leads 3-0 in 3 meetings on hard
Clay
1-0
M. leads 1-0 in 1 meeting on clay
Grass
0-1
G. leads 1-0 in 1 meeting on grass
02/Every meeting
5 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, M. first |
|---|---|---|---|---|---|---|
| Aug 29, 2018 | US OpenGrand Slam, best of 5 | hard | 2nd round | Raonic M. | 6-3, 6-4, 6-4 | 24 v 40 |
| Jan 21, 2017 | Australian OpenGrand Slam, best of 5 | hard | 3rd round | Raonic M. | 6-2, 7-6, 3-6, 6-3 | 3 v 25 |
| Jun 19, 2015 | AEGON ChampionshipsATP500 | grass | quarterfinal | Simon G. | 4-6, 6-3, 7-5 | 8 v 13 |
| Oct 4, 2014 | Rakuten Japan Open Tennis ChampionshipsATP500 | hard | semifinal | Raonic M. | 6-1, 6-4 | 8 v 37 |
| May 30, 2014 | French OpenGrand Slam, best of 5 | clay | 3rd round | Raonic M. | 4-6, 6-3, 2-6, 6-2, 7-5 | 9 v 30 |
A record, never a share of meetings. Main-draw singles since 2013; a meeting ended by retirement is counted with the sets that were played and marked; a walkover is listed and counted in neither column. Raonic M. and Simon G. each carry the table against every opponent faced.