01/By surface
each with its own count, at equal weight
Hard
3-3
Level 3-3 in 6 meetings on hard
Clay
Never on clay
no meeting on this surface
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, K. first |
|---|---|---|---|---|---|---|
| Oct 6, 2022 | Astana OpenATP500 | hard | 2nd round | Khachanov K. | 2-6, 6-3, 6-3 | 18 v 14 |
| Aug 10, 2022 | Canadian OpenMasters 1000 | hard | 2nd round | Cilic M. | 6-3, 6-2 | 28 v 16 |
| Feb 17, 2022 | Qatar Exxon Mobil OpenATP250 | hard | quarterfinal | Khachanov K. | 3-6, 6-3, 6-4 | 27 v 24 |
| Jan 8, 2022 | Adelaide International 1ATP250 | hard | semifinal | Khachanov K. | 7-6, 6-3 | 29 v 30 |
| Oct 28, 2021 | St. Petersburg OpenATP250 | hard | 2nd round | Cilic M. | 6-4, 6-7, 6-4 | 30 v 35 |
| Aug 17, 2018 | Western & Southern Financial Group MastersMasters 1000 | hard | 3rd round | Cilic M. | 7-6, 3-6, 6-4 | 27 v 7 |
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 Cilic M. each carry the table against every opponent faced.