Level, 2 wins each over 4 singles meetings since 2021. Last meeting on 31/07/2025 at National Bank Open - Toronto.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 31/07/2025 | National Bank Open - Toronto | Round 3 | hard | Popyrin | 7-5 4-6 4-6 |
| 11/05/2025 | Internazionali BNL d'Italia - Rome | Round 3 | clay | Medvedev | 4-6 1-6 |
| 30/10/2024 | Rolex Paris Masters - Paris | Round 2 | indoor hard | Popyrin | 6-4 2-6 7-6(4) |
| 28/03/2021 | Miami Open - Miami | Round 3 | hard | Medvedev | 7-6(3) 6-7(7) 6-4 |
| hard | Medvedev 1 - 1 Popyrin |
| clay | Medvedev 1 - 0 Popyrin |
| indoor hard | Medvedev 0 - 1 Popyrin |
| 2025 | Medvedev 1 - 1 Popyrin |
| 2024 | Medvedev 0 - 1 Popyrin |
| 2021 | Medvedev 1 - 0 Popyrin |
294 wins, 108 losses since 2021 (73.1%).
Last matches: V V V D D
146 wins, 150 losses since 2021 (49.3%).
Last matches: D V D V D
Level, 2 wins each over 4 singles meetings since 2021.
On 31/07/2025, at National Bank Open - Toronto (Round 3): Alexei Popyrin won 7-5 4-6 4-6.