D. Medvedev leads the head-to-head 5-2 since 2018 against J-L. Struff, over 7 matches.
| Date | Winner | Score | Event |
| July 3, 2026 | J-L. Struff | 3 - 0 | Wimbledon · 1/16-finals · grass |
| Feb. 25, 2025 | D. Medvedev | 2 - 0 | ATP Dubai · 1/16-finals · hard |
| Feb. 14, 2025 | D. Medvedev | 2 - 0 | Marseille · Quarter-finals · hard |
| July 6, 2024 | D. Medvedev | 3 - 1 | ATP Wimbledon · 1/16-finals · grass |
| June 29, 2021 | D. Medvedev | 3 - 1 | Wimbledon · 1/64-finals · grass |
| June 15, 2021 | J-L. Struff | 2 - 0 | Halle · 1/16-finals · grass |
| Dec. 12, 2019 | D. Medvedev | 2 - 0 | Diriyah Tennis Cup · Quarter-finals · hard |