| TT Cup | 2021/11/24 12:50 | Tsybulin, Sergey v Shkurupii, A. | W | 3-1 |
| TT Cup | 2021/11/04 14:05 | Tsybulin, Sergey v Shkurupii, A. | L | 0-3 |
| TT Cup | 2021/11/03 08:50 | Tsybulin, Sergey v Shkurupii, A. | W | 3-2 |
| TT Cup | 2021/10/28 05:30 | Tsybulin, Sergey v Shkurupii, A. | L | 2-3 |
| TT Cup | 2021/10/27 13:00 | Tsybulin, Sergey v Shkurupii, A. | L | 0-3 |
| TT Cup | 2021/10/24 11:50 | Tsybulin, Sergey v Shkurupii, A. | W | 3-0 |
| TT Cup | 2021/10/23 13:00 | Shkurupii, A. v Tsybulin, Sergey | L | 3-2 |
| TT Cup | 2021/10/21 11:20 | Shkurupii, A. v Tsybulin, Sergey | L | 3-1 |
| TT Cup | 2021/10/20 10:10 | Tsybulin, Sergey v Shkurupii, A. | W | 3-1 |
| TT Cup | 2021/10/13 05:25 | Tsybulin, Sergey v Shkurupii, A. | L | 2-3 |
| TT Cup | 2021/10/07 10:10 | Shkurupii, A. v Tsybulin, Sergey | L | 3-2 |
| TT Cup | 2021/10/06 09:00 | Shkurupii, A. v Tsybulin, Sergey | W | 0-3 |
| TT Cup | 2021/09/23 10:40 | Tsybulin, Sergey v Shkurupii, A. | L | 1-3 |
| TT Cup | 2021/09/22 07:45 | Tsybulin, Sergey v Shkurupii, A. | W | 3-0 |
| TT Cup | 2021/09/19 10:40 | Tsybulin, Sergey v Shkurupii, A. | L | 2-3 |
| TT Cup | 2021/09/18 06:35 | Shkurupii, A. v Tsybulin, Sergey | W | 2-3 |
| TT Cup | 2021/07/08 13:00 | Tsybulin, Sergey v Shkurupii, A. | L | 0-3 |
| TT Cup | 2021/07/07 06:35 | Shkurupii, A. v Tsybulin, Sergey | L | 3-0 |
| TT Cup | 2021/07/01 16:00 | Shkurupii, A. v Tsybulin, Sergey | L | 3-0 |
| TT Cup | 2021/07/01 14:15 | Shkurupii, A. v Tsybulin, Sergey | W | 0-3 |
| TT Cup | 2021/06/30 16:00 | Shkurupii, A. v Tsybulin, Sergey | L | 3-1 |
| TT Cup | 2021/06/30 14:15 | Shkurupii, A. v Tsybulin, Sergey | W | 1-3 |
| TT Cup | 2021/06/24 05:25 | Tsybulin, Sergey v Shkurupii, A. | L | 1-3 |
| TT Cup | 2021/06/03 06:00 | Shkurupii, A. v Tsybulin, Sergey | L | 3-2 |
| TT Cup | 2021/06/02 11:15 | Tsybulin, Sergey v Shkurupii, A. | W | 3-1 |
| TT Cup | 2021/05/24 10:40 | Tsybulin, Sergey v Shkurupii, A. | W | 3-2 |
| TT Cup | 2021/05/24 05:25 | Tsybulin, Sergey v Shkurupii, A. | W | 3-0 |
| TT Cup | 2021/05/18 08:55 | Tsybulin, Sergey v Shkurupii, A. | L | 2-3 |
| TT Cup | 2021/05/17 05:25 | Tsybulin, Sergey v Shkurupii, A. | W | 3-0 |
| TT Cup | 2021/05/13 12:25 | Tsybulin, Sergey v Shkurupii, A. | L | 0-3 |