01/By surface
each with its own count, at equal weight
Hard
1-2
M. leads 2-1 in 3 meetings on hard
Clay
Never on clay
no meeting on this surface
Grass
Never on grass
no meeting on this surface
02/Every meeting
3 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, S. first |
|---|---|---|---|---|---|---|
| Aug 29, 2023 | US OpenGrand Slam, best of 5 | hard | 1st round | Tsitsipas S. | 6-2, 6-3, 6-4 | 7 v 337 |
| Aug 28, 2020 | Western & Southern Financial Group MastersMasters 1000 | hard | semifinal | Raonic M. | 7-6, 6-3 | 6 v 30 |
| Jan 24, 2020 | Australian OpenGrand Slam, best of 5 | hard | 3rd round | Raonic M. | 7-5, 6-4, 7-6 | 6 v 35 |
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. Tsitsipas S. and Raonic M. each carry the table against every opponent faced.