01/By surface
each with its own count, at equal weight
Hard
1-1
Level 1-1 in 2 meetings on hard
Clay
0-2
C. leads 2-0 in 2 meetings on clay
Grass
Never on grass
no meeting on this surface
02/Every meeting
4 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, D. first |
|---|---|---|---|---|---|---|
| Oct 18, 2025 | Nordic OpenATP250 | hard | semifinal | Ruud C. | 6-3, 6-4 | 23 v 12 |
| Feb 9, 2025 | Dallas OpenATP500 | hard | final | Shapovalov D. | 7-6, 6-3 | 54 v 5 |
| May 13, 2022 | Internazionali BNL d'ItaliaMasters 1000 | clay | quarterfinal | Ruud C. | 7-6, 7-5 | 16 v 10 |
| May 22, 2021 | Geneva OpenATP250 | clay | final | Ruud C. | 7-6, 6-4 | 15 v 21 |
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. Shapovalov D. and Ruud C. each carry the table against every opponent faced.