01/By surface
each with its own count, at equal weight
Hard
5-1
D. leads 5-1 in 6 meetings on hard
Clay
1-1
Level 1-1 in 2 meetings on clay
Grass
Never on grass
no meeting on this surface
02/Every meeting
8 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, D. first |
|---|---|---|---|---|---|---|
| Apr 7, 2025 | Monte Carlo MastersMasters 1000 | clay | 1st round | Medvedev D. | 7-5, 4-6, 6-4 | 11 v 25 |
| Feb 18, 2025 | Qatar Exxon Mobil OpenATP500 | hard | 1st round | Medvedev D. | 4-6, 7-5, 6-3 | 6 v 21 |
| Apr 11, 2024 | Monte Carlo MastersMasters 1000 | clay | 3rd round | Khachanov K. | 6-3, 7-5 | 4 v 17 |
| Oct 27, 2023 | Vienna OpenATP500 | hard | quarterfinal | Medvedev D. | 6-3, 3-6, 6-3 | 3 v 16 |
| Mar 31, 2023 | Miami OpenMasters 1000 | hard | semifinal | Medvedev D. | 7-6, 3-6, 6-3 | 5 v 16 |
| Jan 6, 2023 | Adelaide International 1ATP250 | hard | quarterfinal | Medvedev D. | 6-3, 6-3 | 7 v 20 |
| Aug 10, 2019 | Rogers MastersMasters 1000 | hard | semifinal | Medvedev D. | 6-1, 7-6 | 9 v 8 |
| Oct 20, 2018 | Kremlin CupATP250 | hard | semifinal | Khachanov K. | 6-1, 6-7, 6-3 | 21 v 26 |
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 Khachanov K. each carry the table against every opponent faced.