Played: 14 | Djokovic: 9 | Medvedev: 5
2023 Dubai, Semifinals: Medvedev gained 6-4, 6-4
2023 Adelaide, Semifinals: Djokovic gained 6-3, 6-4
2022 ATP Finals, Round Robin: Djokovic gained 6-3, 6-7(5), 7-6(2)
2022 Astana, Semifinals: Djokovic gained 4-6, 7-6(6), retd.
2021 Paris, Final: Djokovic gained 4-6, 6-3, 6-3
2021 US Open, Final: Medvedev gained 6-4, 6-4, 6-4
2021 Australian Open, Final: Djokovic gained 7-5, 6-2, 6-2
2020 ATP Finals, Round Robin: Medvedev gained 6-3, 6-3
2020 ATP Cup, Semifinals: Djokovic gained 6-1, 5-7, 6-4
2019 Cincinnati, Semifinals: Medvedev gained 3-6, 6-3, 6-3
2019 Monte Carlo, Quarterfinals: Medvedev gained 6-3, 4-6, 6-2
2019 Australian Open, Round of 16: Djokovic gained 6-4, 6-7(5), 6-2, 6-3
2017 Eastbourne, Semifinal: Djokovic gained 6-4, 6-4
2017 Davis Cup, Round Robin: Djokovic gained 3-6, 6-4, 6-1, 1-0, retd.
Source: sportstar.thehindu.com