Daniil Medvedev leads the record after 16 meetings.
| Surface | Tsitsipas | Medvedev |
|---|---|---|
| Hard | 4 | 9 |
| Clay | 1 | 2 |
| Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|
| Shanghai Rolex Masters - Shanghai 2026 | R4 | Hard | Medvedev | 6-4 7-5 |
| Qatar ExxonMobil Open - Doha 2026 | R2 | Hard | Tsitsipas | 6-3 6-4 |
| Shanghai Rolex Masters - Shanghai 2024 | R4 | Hard | Medvedev | 7-6(3) 6-3 |
| Erste Bank Open - Vienna 2023 | SF | Hard (Indoor) | Medvedev | 6-4 7-6(6) |
| Internazionali BNL d'Italia - Rome 2023 | SF | Clay | Medvedev | 7-5 7-5 |
| Nitto ATP Finals - Turin 2022 | R5 | Hard (Indoor) | Tsitsipas | 6-3 6-7(11) 7-6(1) |
| Western & Southern Open - Cincinnati 2022 | SF | Hard | Tsitsipas | 7-6(6) 3-6 6-3 |
| Australian Open - Melbourne 2022 | SF | Hard | Medvedev | 7-6(5) 4-6 6-4 6-1 |
| French Open - Paris 2021 | QF | Clay | Tsitsipas | 6-3 7-6(3) 7-5 |
| Australian Open - Melbourne 2021 | SF | Hard | Medvedev | 6-4 6-2 7-5 |
| Nitto ATP Finals - London 2019 | R5 | Hard (Indoor) | Tsitsipas | 7-6(5) 6-4 |
| Shanghai Rolex Masters - Shanghai 2019 | SF | Hard | Medvedev | 7-6(5) 7-5 |
| Monte-Carlo Rolex Masters - Monte-Carlo 2019 | R3 | Clay | Medvedev | 6-2 1-6 6-4 |
| Swiss Indoors Basel - Basel 2018 | QF | Hard (Indoor) | Medvedev | 6-4 3-6 6-3 |
| U.S. Open - New York 2018 | R2 | Hard | Medvedev | 6-4 6-3 4-6 6-3 |
| Miami Open - Miami 2018 | R1 | Hard | Medvedev | 2-6 6-4 6-2 |
Meetings are the ones on our record. Older matches may be missing.
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