01/By surface
each with its own count, at equal weight
Hard
0-4
D. leads 4-0 in 4 meetings on hard
Clay
2-0
S. leads 2-0 in 2 meetings on clay
Grass
Never on grass
no meeting on this surface
02/Every meeting
6 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, S. first |
|---|---|---|---|---|---|---|
| Mar 5, 2026 | BNP Paribas OpenMasters 1000 | hard | 1st round | Shapovalov D. | 6-2, 3-6, 6-4 | 43 v 39 |
| Mar 23, 2024 | Miami OpenMasters 1000 | hard | 2nd round | Shapovalov D. | 6-2, 6-4 | 11 v 126 |
| Apr 20, 2023 | Barcelona OpenATP500 | clay | 3rd round | Tsitsipas S. | 6-3, 6-2 | 5 v 28 |
| Mar 27, 2019 | Sony Ericsson OpenMasters 1000 | hard | 4th round | Shapovalov D. | 4-6, 6-3, 7-6 | 10 v 23 |
| Apr 16, 2018 | Monte Carlo MastersMasters 1000 | clay | 1st round | Tsitsipas S. | 6-3, 6-4 | 71 v 45 |
| Jan 15, 2018 | Australian OpenGrand Slam, best of 5 | hard | 1st round | Shapovalov D. | 6-1, 6-3, 7-6 | 82 v 50 |
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 Shapovalov D. each carry the table against every opponent faced.