Jannik Sinner leads the record after 18 meetings.
| Surface | Medvedev | Sinner |
|---|---|---|
| Hard | 6 | 10 |
| Clay | 0 | 1 |
| Grass | 1 | 0 |
| Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|
| Internazionali BNL d'Italia - Rome 2026 | SF | Clay | Sinner | 6-2 5-7 6-4 |
| BNP Paribas Open - Indian Wells 2026 | F | Hard | Sinner | 7-6(6) 7-6(4) |
| Nitto ATP Finals - Turin 2024 | R5 | Hard (Indoor) | Sinner | 6-3 6-4 |
| Shanghai Rolex Masters - Shanghai 2024 | QF | Hard | Sinner | 6-1 6-4 |
| U.S. Open - New York 2024 | QF | Hard | Sinner | 6-2 1-6 6-1 6-4 |
| Wimbledon - London 2024 | QF | Grass | Medvedev | 6-7(7) 6-4 7-6(4) 2-6 6-3 |
| Miami Open - Miami 2024 | SF | Hard | Sinner | 6-1 6-2 |
| Australian Open - Melbourne 2024 | F | Hard | Sinner | 3-6 3-6 6-4 6-4 6-3 |
| Nitto ATP Finals - Turin 2023 | SF | Hard (Indoor) | Sinner | 6-3 6-7(4) 6-1 |
| Nitto ATP Finals - Turin 2023 | SF | Hard (Indoor) | Sinner | 6-3 6-7(4) 6-1 |
| Erste Bank Open - Vienna 2023 | F | Hard (Indoor) | Sinner | 7-6(7) 4-6 6-3 |
| China Open - Beijing 2023 | F | Hard | Sinner | 7-6(2) 7-6(2) |
| Miami Open - Miami 2023 | F | Hard | Medvedev | 7-5 6-3 |
| ABN AMRO World Tennis Tournament - Rotterdam 2023 | F | Hard (Indoor) | Medvedev | 5-7 6-2 6-2 |
| Erste Bank Open - Vienna 2022 | QF | Hard (Indoor) | Medvedev | 6-4 6-2 |
| Nitto ATP Finals - Turin 2021 | R5 | Hard (Indoor) | Medvedev | 6-0 6-7(5) 7-6(8) |
| Open 13 Provence - Marseille 2021 | QF | Hard (Indoor) | Medvedev | 6-2 6-4 |
| Open 13 Provence - Marseille 2020 | R2 | Hard (Indoor) | Medvedev | 1-6 6-1 6-2 |
Meetings are the ones on our record. Older matches may be missing.
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