J. Sinner leads the head-to-head 9-5 since 2018 against N. Djokovic, over 14 matches.
| Date | Winner | Score | Event |
|---|
| July 10, 2026 | J. Sinner | 3 - 0 | Wimbledon · Semi-finals · grass |
| Jan. 30, 2026 | N. Djokovic | 3 - 2 | Australian Open · Semi-finals · hard |
| Oct. 16, 2025 | J. Sinner | 2 - 0 | Six Kings Slam · Semi-finals · hard |
| July 11, 2025 | J. Sinner | 3 - 0 | Wimbledon · Semi-finals · grass |
| June 6, 2025 | J. Sinner | 3 - 0 | French Open · Semi-finals · clay |
| Oct. 17, 2024 | J. Sinner | 2 - 1 | Six Kings Slam · Semi-finals · hard |
| Oct. 13, 2024 | J. Sinner | 2 - 0 | ATP Shanghai · Final · hard |
| Jan. 26, 2024 | J. Sinner | 3 - 1 | ATP Australian Open · Semi-finals · hard |
| Nov. 25, 2023 | J. Sinner | 2 - 1 | ATP Davis Cup - World Group |
| Nov. 19, 2023 | N. Djokovic | 2 - 0 | ATP Finals - Turin · Final · hard |
| Nov. 14, 2023 | J. Sinner | 2 - 1 | ATP Finals - Turin · hard |
| July 14, 2023 | N. Djokovic | 3 - 0 | ATP Wimbledon · Semi-finals · grass |
| July 5, 2022 | N. Djokovic | 3 - 2 | Wimbledon · Quarter-finals · grass |
| Jan. 29, 2021 | N. Djokovic | 1 - 0 | Exhibition A Day at the Drive · hard |