Grigor Dimitrov (Bulgaria) 2 - 5 Stefanos Tsitsipas (Greece)
| Date | Tournament | Rnd | Winner | Score |
|---|---|---|---|---|
| 04 Nov 2023 |
Rolex Paris Masters
Paris,
France
ATP Tour Masters, Hard |
SF |
Grigor Dimitrov
(BUL  )
|
6-3 6-7(1) 7-6(3) |
| 11 May 2022 |
Internazionali BNL d'Italia
Rome,
Italy
ATP Tour Masters, Clay |
R32 |
Stefanos Tsitsipas
(GRE  )
|
3-6 7-5 6-7(4) |
| 05 May 2022 |
Mutua Madrid Open
Madrid,
Spain
ATP Tour Masters, Clay |
R16 |
Stefanos Tsitsipas
(GRE )
|
3-6 4-6 |
| 22 Apr 2022 |
Barcelona Open Banc Sabadell
Barcelona,
Spain
ATP Tour 500, Clay |
R16 |
Stefanos Tsitsipas
(GRE )
|
1-6 4-6 |
| 25 Oct 2021 |
Erste Bank Open 500
Vienna,
Austria
ATP Tour 500, Hard |
R32 |
Stefanos Tsitsipas
(GRE )
|
6-7(6) 4-6 |
| 29 Oct 2020 |
Erste Bank Open 500
Vienna,
Austria
ATP Tour 500, Hard |
R16 |
Grigor Dimitrov
(BUL )
|
6-7(5) 6-4 6-3 |
| 05 Oct 2020 |
Roland Garros
Paris,
France
Grand Slam, Clay |
R16 |
Stefanos Tsitsipas
(GRE )
|
3-6 6-7(9) 2-6 |