01/By surface
each with its own count, at equal weight
Hard
2-0
S. leads 2-0 in 2 meetings on hard
Clay
Never on clay
no meeting on this surface
Grass
Never on grass
no meeting on this surface
02/Every meeting
2 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, S. first |
|---|---|---|---|---|---|---|
| Oct 19, 2022 | Stockholm OpenATP250 | hard | 2nd round | Tsitsipas S. | 7-6, 7-6 | 5 v 33 |
| Sep 3, 2020 | US OpenGrand Slam, best of 5 | hard | 2nd round | Tsitsipas S. | 7-6, 6-3, 6-4 | 6 v 168 |
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 Cressy M. each carry the table against every opponent faced.