D. Medvedev leads the head-to-head 3-1 since 2018 against M. Cilic, over 4 matches.
| Surface | D. Medvedev | M. Cilic |
|---|---|---|
| Grass | 3 | 0 |
| Clay | 0 | 1 |
| Date | Winner | Score | Event |
|---|---|---|---|
| June 29, 2026 | D. Medvedev | 3 - 0 | Wimbledon · 1/64-finals · grass |
| June 13, 2026 | D. Medvedev | 2 - 1 | Hertogenbosch · Quarter-finals · grass |
| May 30, 2022 | M. Cilic | 3 - 0 | French Open · 1/8-finals · clay |
| July 3, 2021 | D. Medvedev | 3 - 2 | Wimbledon · 1/16-finals · grass |