01/By surface
each with its own count, at equal weight
Hard
3-3
Level 3-3 in 6 meetings on hard
Clay
1-0
S. leads 1-0 in 1 meeting on clay
Grass
Never on grass
no meeting on this surface
02/Every meeting
7 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, S. first |
|---|---|---|---|---|---|---|
| Feb 13, 2019 | ABN AMRO World Tennis TournamentATP500 | hard | 2nd round | Wawrinka S. | 6-4, 7-6 | 68 v 14 |
| Jan 17, 2019 | Australian OpenGrand Slam, best of 5 | hard | 2nd round | Raonic M. | 6-7, 7-6, 7-6, 7-6 | 59 v 17 |
| Sep 1, 2018 | US OpenGrand Slam, best of 5 | hard | 3rd round | Raonic M. | 7-6, 6-4, 6-3 | 101 v 24 |
| Jan 25, 2016 | Australian OpenGrand Slam, best of 5 | hard | 4th round | Raonic M. | 6-4, 6-3, 5-7, 4-6, 6-3 | 4 v 14 |
| Feb 14, 2015 | ABN AMRO World Tennis TournamentATP500 | hard | semifinal | Wawrinka S. | 7-6, 7-6 | 8 v 6 |
| Apr 18, 2014 | Monte Carlo MastersMasters 1000 | clay | quarterfinal | Wawrinka S. | 7-6, 6-2 | 3 v 10 |
| Oct 10, 2013 | Shanghai MastersMasters 1000 | hard | 3rd round | Wawrinka S. | 7-6, 6-4 | 8 v 11 |
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. Wawrinka S. and Raonic M. each carry the table against every opponent faced.