01/By surface
each with its own count, at equal weight
Hard
0-1
D. leads 1-0 in 1 meeting on hard
Clay
1-0
M. leads 1-0 in 1 meeting on clay
Grass
0-3
D. leads 3-0 in 3 meetings on grass
02/Every meeting
5 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, M. first |
|---|---|---|---|---|---|---|
| Jun 29, 2026 | WimbledonGrand Slam, best of 5 | grass | 1st round | Medvedev D. | 6-1, 6-2, 6-4 | 62 v 9 |
| Jun 13, 2026 | Rosmalen Grass Court ChampionshipsATP250 | grass | quarterfinal | Medvedev D. | 6-2, 3-6, 6-1 | 47 v 8 |
| May 30, 2022 | French OpenGrand Slam, best of 5 | clay | 4th round | Cilic M. | 6-2, 6-3, 6-2 | 23 v 2 |
| Jul 3, 2021 | WimbledonGrand Slam | grass | 3rd round | Medvedev D. | 6-7, 3-6, 6-3, 6-3, 6-2 | 37 v 2 |
| Aug 2, 2019 | Citi OpenATP500 | hard | quarterfinal | Medvedev D. | 6-4, 7-6 | 17 v 10 |
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. Cilic M. and Medvedev D. each carry the table against every opponent faced.