D. Medvedev leads the head-to-head 12-3 since 2018 against A. Zverev, over 15 matches.
ELO is computed per surface from results since 2018; the win-loss pair is that surface's record.
| Date | Winner | Score | Event |
| Oct. 31, 2025 | A. Zverev | 2 - 1 | Paris · Quarter-finals · hard |
| Sept. 29, 2025 | D. Medvedev | 2 - 0 | Beijing · Quarter-finals · hard |
| June 21, 2025 | D. Medvedev | 2 - 1 | Halle · Semi-finals · grass |
| Jan. 26, 2024 | D. Medvedev | 3 - 2 | ATP Australian Open · Semi-finals · hard |
| Nov. 15, 2023 | D. Medvedev | 2 - 0 | ATP Finals - Turin · hard |
| Oct. 3, 2023 | D. Medvedev | 2 - 0 | ATP Beijing · Semi-finals · hard |
| Aug. 17, 2023 | A. Zverev | 2 - 1 | ATP Cincinnati · 1/8-finals · hard |
| May 16, 2023 | D. Medvedev | 2 - 0 | ATP Rome · 1/8-finals · clay |
| April 13, 2023 | D. Medvedev | 2 - 1 | ATP Monte Carlo · 1/8-finals · clay |
| March 14, 2023 | D. Medvedev | 2 - 1 | ATP Indian Wells · 1/8-finals · hard |
| Dec. 8, 2022 | D. Medvedev | 2 - 0 | Diriyah Tennis Cup · Quarter-finals · hard |
| Nov. 21, 2021 | A. Zverev | 2 - 0 | Finals - Turin · Final · hard |
| Nov. 16, 2021 | D. Medvedev | 2 - 1 | Finals - Turin · hard |
| Nov. 6, 2021 | D. Medvedev | 2 - 0 | Paris · Semi-finals · hard |
| Oct. 13, 2019 | D. Medvedev | 2 - 0 | Shanghai · Final · hard |