Grigor Dimitrov (Bulgaria) 5 - 1 Karen Khachanov
| Date | Tournament | Rnd | Winner | Score |
|---|---|---|---|---|
| 23 Mar 2025 |
Miami Open
Miami, Florida,
USA
ATP Tour Masters, Hard |
R32 |
Grigor Dimitrov
(BUL  )
|
6-7{3} 6-4 7-5 |
| 01 Nov 2024 |
Rolex Paris Masters
Paris,
France
ATP Tour Masters, Hard |
Q | Karen Khachanov | 2-6 3-6 |
| 10 Feb 2024 |
Open 13
Marseille,
France
ATP Tour 250, Hard |
SF |
Grigor Dimitrov
(BUL )
|
6-7(3) 6-4 7-6(5) |
| 09 Oct 2023 |
Shanghai Rolex Masters
Shanghai,
China
ATP Tour Masters, Hard |
R32 |
Grigor Dimitrov
(BUL )
|
7-6(6) 6-4 |
| 03 Nov 2021 |
Rolex Paris Masters
Paris,
France
ATP Tour Masters, Hard |
R32 |
Grigor Dimitrov
(BUL )
|
4-6 6-2 6-0 |
| 27 Oct 2020 |
Erste Bank Open 500
Vienna,
Austria
ATP Tour 500, Hard |
R32 |
Grigor Dimitrov
(BUL )
|
7-6(6) 6-3 |