[28] Karen Khachanov 3-6,2-6 Stefanos Tsitsipas [3] 2021-08-12 15:00
Stadium: Stadium Round: 26 Ground: Hardcourt outdoor
Head to Head
| ATP Rotterdam | 2021/03/05 12:00 | Karen Khachanov v Stefanos Tsitsipas | 6-4,3-6,5-7 |
| Boodles Challenge | 2019/06/26 15:05 | Stefanos Tsitsipas v Karen Khachanov | 6-3,3-6,8-10 |
| ATP Shanghai | 2018/10/10 06:40 | Karen Khachanov v Stefanos Tsitsipas | 4-6,6-7 |
| ATP Shanghai | 2017/10/09 07:40 | Stefanos Tsitsipas v Karen Khachanov | 7-5,6-3 |
Home History
| ATP Toronto | 2021/08/11 17:30 | Aslan Karatsev v Karen Khachanov | 6-7,4-6 |
| ATP Toronto | 2021/08/10 15:00 | Cameron Norrie v Karen Khachanov | 4-6,7-5,4-6 |
| Olympics 2020 - Men | 2021/08/01 07:40 | Alexander Zverev v Karen Khachanov | 6-3,6-1 |
| Olympics 2020 - Men | 2021/07/30 06:00 | Karen Khachanov v Pablo Carreno Busta | 6-3,6-3 |
| Olympics 2020 - Men | 2021/07/29 06:00 | Karen Khachanov v Ugo Humbert | 7-6,4-6,6-3 |
| Olympics 2020 - Men | 2021/07/28 03:15 | Diego Schwartzman v Karen Khachanov | 1-6,6-2,1-6 |
| Olympics 2020 - Men | 2021/07/27 06:20 | James Duckworth v Karen Khachanov | 5-7,1-6 |
| Olympics 2020 - Men | 2021/07/25 02:00 | Yoshihito Nishioka v Karen Khachanov | 6-3,1-6,2-6 |
Away History
| ATP Toronto | 2021/08/10 23:50 | Ugo Humbert v Stefanos Tsitsipas | 3-6,7-6,1-6 |
| Olympics 2020 - Men | 2021/07/28 04:10 | Ugo Humbert v Stefanos Tsitsipas | 2-6,7-6,6-2 |
| Olympics 2020 - Men | 2021/07/27 02:00 | Frances Tiafoe v Stefanos Tsitsipas | 3-6,4-6 |
| Olympics 2020 - Men | 2021/07/25 07:50 | Philipp Kohlschreiber v Stefanos Tsitsipas | 3-6,6-3,3-6 |
| ATP Hamburg | 2021/07/16 12:00 | Stefanos Tsitsipas v Filip Krajinovic | 6-3,1-6,3-6 |
| ATP Hamburg | 2021/07/14 15:15 | Stefanos Tsitsipas v Dominik Koepfer | 7-6,6-3 |
| Wimbledon | 2021/06/28 13:50 | Stefanos Tsitsipas v Frances Tiafoe | 4-6,4-6,3-6 |
| French Open | 2021/06/13 13:00 | Novak Djokovic v Stefanos Tsitsipas | 6-7,2-6,6-3,6-2,6-4 |