| TT Cup | 2020/08/23 11:15 | Tsybulin, Sergey v May, Ivan | L | 3-2 |
| TT Cup | 2020/08/22 07:10 | Tsybulin, Sergey v May, Ivan | L | 3-1 |
| TT Cup | 2020/07/24 01:05 | Tsybulin, Sergey v May, Ivan | L | 3-0 |
| TT Cup | 2020/07/22 21:05 | May, Ivan v Tsybulin, Sergey | W | 3-1 |
| TT Cup | 2020/07/21 06:30 | May, Ivan v Tsybulin, Sergey | W | 3-1 |
| TT Cup | 2020/07/20 10:00 | May, Ivan v Tsybulin, Sergey | W | 3-1 |
| TT Cup | 2020/07/07 14:50 | May, Ivan v Tsybulin, Sergey | L | 0-3 |
| TT Cup | 2020/07/06 14:50 | May, Ivan v Tsybulin, Sergey | L | 0-3 |
| TT Cup | 2020/09/19 06:00 | Teterya, Yuriy v May, Ivan | L | 3-0 |
| TT Cup | 2020/09/05 12:00 | Telnoy, Nikolay v May, Ivan | W | 1-3 |
| TT Cup | 2020/09/05 10:50 | Yaremchuk, Dmytro v May, Ivan | W | 2-3 |
| TT Cup | 2020/09/05 09:05 | Tkachenko, Oleksandr v May, Ivan | W | 2-3 |
| TT Cup | 2020/09/05 07:55 | May, Ivan v Tkachenko, Oleksandr | W | 3-0 |
| TT Cup | 2020/09/05 06:45 | May, Ivan v Yaremchuk, Dmytro | W | 3-0 |
| TT Cup | 2020/09/05 05:35 | May, Ivan v Telnoy, Nikolay | L | 2-3 |
| TT Cup | 2020/09/04 11:25 | May, Ivan v Telnoy, Nikolay | L | 1-3 |
| TT Cup | 2020/09/19 04:50 | 디두크, 빅터 v Tsybulin, Sergey | W | 1-3 |
| TT Cup | 2020/09/17 12:25 | Krutko, Aleksey v Tsybulin, Sergey | W | 2-3 |
| TT Cup | 2020/09/17 11:15 | Oleskevych, Olexander v Tsybulin, Sergey | L | 3-2 |
| TT Cup | 2020/09/17 09:30 | Boiko, Serhii v Tsybulin, Sergey | L | 3-0 |
| TT Cup | 2020/09/17 07:10 | 디두크, 빅터 v Tsybulin, Sergey | L | 3-1 |
| TT Cup | 2020/09/17 04:50 | Kovalchuk, Nazar v Tsybulin, Sergey | L | 3-2 |
| TT Cup | 2020/09/16 12:25 | 디두크, 빅터 v Tsybulin, Sergey | L | 3-1 |
| TT Cup | 2020/09/16 11:15 | Oleskevych, Olexander v Tsybulin, Sergey | W | 2-3 |