Novak Djokovic leads the record after 16 meetings.
| Surface | Medvedev | Djokovic |
|---|---|---|
| Hard | 4 | 10 |
| Clay | 1 | 0 |
| Grass | 0 | 1 |
| Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|
| China Open - Beijing 2026 | SF | Hard | Djokovic | 7-5 5-3 def. |
| U.S. Open - New York 2023 | F | Hard | Djokovic | 6-3 7-6(5) 6-3 |
| Dubai Duty Free Tennis Championships - Dubai 2023 | SF | Hard | Medvedev | 6-4 6-4 |
| Adelaide International 1 - Adelaide 2023 | SF | Hard | Djokovic | 6-3 6-4 |
| Nitto ATP Finals - Turin 2022 | R5 | Hard (Indoor) | Djokovic | 6-3 6-7(5) 7-6(2) |
| Astana Open - Astana 2022 | SF | Hard (Indoor) | Djokovic | 4-6 7-6(6) 0-0 ret. |
| Rolex Paris Masters - Paris 2021 | F | Hard (Indoor) | Djokovic | 4-6 6-3 6-3 |
| U.S. Open - New York 2021 | F | Hard | Medvedev | 6-4 6-4 6-4 |
| Australian Open - Melbourne 2021 | F | Hard | Djokovic | 7-5 6-2 6-2 |
| Nitto ATP Finals - London 2020 | R5 | Hard (Indoor) | Medvedev | 6-3 6-3 |
| ATP Cup - Brisbane, Perth, Sydney 2020 | SF | Hard | Djokovic | 6-1 5-7 6-4 |
| Western & Southern Open - Cincinnati 2019 | SF | Hard | Medvedev | 3-6 6-3 6-3 |
| Monte-Carlo Rolex Masters - Monte-Carlo 2019 | QF | Clay | Medvedev | 6-3 4-6 6-2 |
| Australian Open - Melbourne 2019 | R4 | Hard | Djokovic | 6-4 6-7(5) 6-2 6-3 |
| AEGON International - Eastbourne 2017 | SF | Grass | Djokovic | 6-4 6-4 |
| Davis Cup, World Group, 1R, SRB-RUS 4-1 2017 | R14 | Hard (Indoor) | Djokovic | 3-6 6-4 6-1 1-0 ret. |
Meetings are the ones on our record. Older matches may be missing.
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