01/By surface
each with its own count, at equal weight
Hard
1-1
Level 1-1 in 2 meetings on hard
Clay
1-3
C. leads 3-1 in 4 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 |
|---|---|---|---|---|---|---|
| Apr 28, 2026 | Mutua Madrid OpenMasters 1000 | clay | 4th round | Ruud C. | 6-7, 7-6, 7-6 | 80 v 15 |
| Apr 21, 2024 | Barcelona OpenATP500 | clay | final | Ruud C. | 7-5, 6-3 | 7 v 6 |
| Apr 14, 2024 | Monte Carlo MastersMasters 1000 | clay | final | Tsitsipas S. | 6-1, 6-4 | 12 v 10 |
| Feb 24, 2024 | Los Cabos OpenATP250 | hard | semifinal | Ruud C. | 6-4, 7-6 | 11 v 12 |
| Aug 13, 2021 | Canadian OpenMasters 1000 | hard | quarterfinal | Tsitsipas S. | 6-1, 6-4 | 3 v 12 |
| May 6, 2021 | Mutua Madrid OpenMasters 1000 | clay | 3rd round | Ruud C. | 7-6, 6-4 | 5 v 22 |
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 Ruud C. each carry the table against every opponent faced.