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, K. first |
|---|---|---|---|---|---|---|
| May 13, 2026 | Internazionali BNL d'ItaliaMasters 1000 | clay | quarterfinal | Ruud C. | 6-1, 1-6, 6-2 | 15 v 25 |
| Aug 2, 2025 | Canadian OpenMasters 1000 | hard | 4th round | Khachanov K. | 6-4, 7-5 | 16 v 13 |
| Sep 9, 2022 | US OpenGrand Slam, best of 5 | hard | semifinal | Ruud C. | 7-6, 6-2, 5-7, 6-2 | 31 v 7 |
| Sep 14, 2020 | Internazionali BNL d'ItaliaMasters 1000 | clay | 1st round | Ruud C. | 6-3, 3-6, 6-1 | 16 v 34 |
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. Khachanov K. and Ruud C. each carry the table against every opponent faced.