01/By surface
each with its own count, at equal weight
Hard
1-0
D. leads 1-0 in 1 meeting on hard
Clay
0-1
C. leads 1-0 in 1 meeting on clay
Grass
1-0
D. leads 1-0 in 1 meeting on grass
02/Every meeting
3 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, D. first |
|---|---|---|---|---|---|---|
| May 1, 2025 | Mutua Madrid OpenMasters 1000 | clay | quarterfinal | Ruud C. | 6-3, 7-5 | 10 v 15 |
| Nov 20, 2021 | Masters CupMasters Cup | hard | semifinal | Medvedev D. | 6-4, 6-2 | 2 v 8 |
| Jun 24, 2021 | Mallorca ChampionshipsATP250 | grass | quarterfinal | Medvedev D. | 7-5, 6-1 | 2 v 14 |
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. Medvedev D. and Ruud C. each carry the table against every opponent faced.