| TT Cup | 2021/10/20 10:10 | Tsybulin, Sergey v Shkurupii, A. | L | 3-1 |
| TT Cup | 2021/10/13 05:25 | Tsybulin, Sergey v Shkurupii, A. | W | 2-3 |
| TT Cup | 2021/10/07 10:10 | Shkurupii, A. v Tsybulin, Sergey | W | 3-2 |
| TT Cup | 2021/10/06 09:00 | Shkurupii, A. v Tsybulin, Sergey | L | 0-3 |
| TT Cup | 2021/09/23 10:40 | Tsybulin, Sergey v Shkurupii, A. | W | 1-3 |
| TT Cup | 2021/09/22 07:45 | Tsybulin, Sergey v Shkurupii, A. | L | 3-0 |
| TT Cup | 2021/09/19 10:40 | Tsybulin, Sergey v Shkurupii, A. | W | 2-3 |
| TT Cup | 2021/09/18 06:35 | Shkurupii, A. v Tsybulin, Sergey | L | 2-3 |
| TT Cup | 2021/10/21 09:00 | 슈체르바크, 데니스 v Shkurupii, A. | W | 2-3 |
| TT Cup | 2021/10/21 06:40 | Boiko, Serhii v Shkurupii, A. | W | 1-3 |
| TT Cup | 2021/10/21 05:30 | Krutko, Aleksey v Shkurupii, A. | W | 2-3 |
| TT Cup | 2021/10/20 10:10 | Tsybulin, Sergey v Shkurupii, A. | L | 3-1 |
| TT Cup | 2021/10/20 07:50 | Krutko, Aleksey v Shkurupii, A. | L | 3-0 |
| TT Cup | 2021/10/20 06:05 | Boiko, Serhii v Shkurupii, A. | W | 1-3 |
| TT Cup | 2021/10/20 04:55 | 슈체르바크, 데니스 v Shkurupii, A. | L | 3-0 |
| TT Cup | 2021/10/13 13:00 | Baklykov, Andrey v Shkurupii, A. | L | 3-2 |
| TT Cup | 2021/10/21 09:35 | Krutko, Aleksey v Tsybulin, Sergey | L | 3-0 |
| TT Cup | 2021/10/21 07:15 | Levadniy, Aleksandr v Tsybulin, Sergey | W | 1-3 |
| TT Cup | 2021/10/21 04:55 | Boiko, Serhii v Tsybulin, Sergey | W | 0-3 |
| TT Cup | 2021/10/20 10:45 | Tsybulin, Sergey v Krutko, Aleksey | W | 3-2 |
| TT Cup | 2021/10/20 10:10 | Tsybulin, Sergey v Shkurupii, A. | W | 3-1 |
| TT Cup | 2021/10/20 09:00 | 슈체르바크, 데니스 v Tsybulin, Sergey | L | 3-2 |
| TT Cup | 2021/10/20 07:15 | Boiko, Serhii v Tsybulin, Sergey | W | 2-3 |
| TT Cup | 2021/10/20 05:30 | Krutko, Aleksey v Tsybulin, Sergey | L | 3-2 |