J. Sinner leads the head-to-head 11-5 since 2018 against D. Medvedev, over 16 matches.
| Date | Winner | Score | Event |
| May 16, 2026 | J. Sinner | 2 - 1 | Rome · Semi-finals · clay |
| March 15, 2026 | J. Sinner | 2 - 0 | ATP Indian Wells · Final · hard |
| Nov. 14, 2024 | J. Sinner | 2 - 0 | ATP Finals - Turin · hard |
| Oct. 16, 2024 | J. Sinner | 2 - 0 | Six Kings Slam · Quarter-finals · hard |
| Oct. 10, 2024 | J. Sinner | 2 - 0 | ATP Shanghai · Quarter-finals · hard |
| Sept. 5, 2024 | J. Sinner | 3 - 1 | ATP US Open · Quarter-finals · hard |
| July 9, 2024 | D. Medvedev | 3 - 2 | ATP Wimbledon · Quarter-finals · grass |
| March 29, 2024 | J. Sinner | 2 - 0 | ATP Miami · Semi-finals · hard |
| Jan. 28, 2024 | J. Sinner | 3 - 2 | ATP Australian Open · Final · hard |
| Nov. 18, 2023 | J. Sinner | 2 - 1 | ATP Finals - Turin · Semi-finals · hard |
| Oct. 29, 2023 | J. Sinner | 2 - 1 | ATP Vienna · Final · hard |
| Oct. 4, 2023 | J. Sinner | 2 - 0 | ATP Beijing · Final · hard |
| April 2, 2023 | D. Medvedev | 2 - 0 | ATP Miami · Final · hard |
| Feb. 19, 2023 | D. Medvedev | 2 - 1 | Rotterdam · Final · hard |
| Oct. 28, 2022 | D. Medvedev | 2 - 0 | Vienna · Quarter-finals · hard |
| Nov. 18, 2021 | D. Medvedev | 2 - 1 | Finals - Turin · hard |