[20] Grigor Dimitrov 3-6,4-6 Stefanos Tsitsipas [5] 2022-05-05 15:30
Stadium: Arantxa Sanchez Stadium Round: 26 Ground: Clay
Head to Head
| ATP Barcelona | 2022/04/22 12:55 | Stefanos Tsitsipas v Grigor Dimitrov | 6-1,6-4 |
| ATP Vienna | 2021/10/26 14:05 | Stefanos Tsitsipas v Grigor Dimitrov | 7-6,6-4 |
| ATP Vienna | 2020/10/29 18:50 | Stefanos Tsitsipas v Grigor Dimitrov | 7-6,4-6,3-6 |
| French Open | 2020/10/05 10:45 | Grigor Dimitrov v Stefanos Tsitsipas | 3-6,6-7,2-6 |
| Boodles Challenge | 2018/06/26 13:30 | Grigor Dimitrov v Stefanos Tsitsipas | 7-6,6-1 |