Grigor Dimitrov (Bulgaria) 3 - 9 Daniil Medvedev
| Date | Tournament | Rnd | Winner | Score |
|---|---|---|---|---|
| 29 Oct 2025 |
Rolex Paris Masters
Paris,
France
ATP Tour Masters, Hard |
R32 | Daniil Medvedev | w.o. |
| 07 Jul 2024 |
The Championships
Wimbledon,
Great Britain
Grand Slam, Grass |
R16 | Daniil Medvedev | 3-5 ret. |
| 13 Mar 2024 |
BNP Paribas Open
Indian Wells, CA,
USA
ATP Tour Masters, Hard |
R16 | Daniil Medvedev | 4-6 4-6 |
| 01 Nov 2023 |
Rolex Paris Masters
Paris,
France
ATP Tour Masters, Hard |
R32 |
Grigor Dimitrov
(BUL  )
|
6-3 6-7(4) 7-6(2) |
| 26 Oct 2023 |
Erste Bank Open 500
Vienna,
Austria
ATP Tour 500, Hard |
R16 | Daniil Medvedev | 6-3 2-6 4-6 |
| 18 Feb 2023 |
ABN Amro
Rotterdam,
The Netherlands
ATP Tour 500, Hard |
SF | Daniil Medvedev | 1-6 2-6 |
| 29 Oct 2022 |
Erste Bank Open 500
Vienna,
Austria
ATP Tour 500, Hard |
SF | Daniil Medvedev | 4-6 2-6 |
| 13 Oct 2021 |
BNP Paribas Open
Indian Wells, CA,
USA
ATP Tour Masters, Hard |
R16 |
Grigor Dimitrov
(BUL )
|
4-6 6-4 6-3 |
| 19 Aug 2021 |
Cincinnati Open
Cincinnati, OH,
USA
ATP Tour Masters, Hard |
R16 | Daniil Medvedev | 3-6 3-6 |
| 06 Sep 2019 |
US Open
Flushing Meadows, NY,
USA
Grand Slam, Hard |
SF | Daniil Medvedev | 6-7(5) 4-6 3-6 |
| 03 Aug 2017 |
Mubadala Citi DC Open
Washington, DC,
USA
ATP Tour 500, Hard |
R16 | Daniil Medvedev | 4-6 2-6 |
| 23 Jun 2017 |
HSBC Championships
London / Queen`s Club,
Great Britain
ATP Tour 500, Grass |
Q |
Grigor Dimitrov
(BUL )
|
6-3 3-6 6-3 |