| TT Cup | 05/28 14:05 | - | Yevhenii Cherkashyn v Mart Martin | D | 2-2 | |
| TT Cup | 05/28 12:45 | - | Mart Martin v Yevhenii Cherkashyn | - | Cancelled | |
| TT Cup | 05/28 12:15 | - | Yevhenii Cherkashyn v Markus-Oliver Annuk | W | 3-2 | |
| TT Cup | 05/28 11:15 | - | Yevhenii Cherkashyn v Martin Mart | W | 3-0 | |
| TT Cup | 05/28 10:15 | - | Yevhenii Cherkashyn v Heiki Magi | L | 2-3 | |
| TT Cup | 05/27 13:15 | - | Heiki Magi v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 05/27 12:45 | - | Mart Martin v Yevhenii Cherkashyn | L | 3-0 | |
| TT Cup | 05/27 11:45 | - | Yevhenii Cherkashyn v Toomas Talumets | L | 1-3 | |
| TT Cup | 05/27 10:15 | - | Heiki Magi v Yevhenii Cherkashyn | L | 3-1 | |
| TT Cup | 05/24 18:55 | - | Yevhenii Cherkashyn v Oliver Ollmann | W | 3-0 | |
| TT Cup | 05/24 17:15 | - | Oliver Ollmann v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 05/24 16:45 | - | Toivo Tuisk v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 05/24 15:45 | - | Yevhenii Cherkashyn v Stanislav Kruti | W | 3-1 | |
| TT Cup | 05/02 13:15 | - | Vootele Vaher v Yevhenii Cherkashyn | L | 3-1 | |
| TT Cup | 05/02 12:45 | - | Yevhenii Cherkashyn v Vootele Vaher | L | 0-3 | |
| TT Cup | 05/02 11:15 | - | Jaanus Lokotar v Yevhenii Cherkashyn | W | 1-3 | |
| TT Cup | 05/02 10:45 | - | Rene Riomar v Yevhenii Cherkashyn | L | 3-2 | |
| TT Cup | 04/30 13:50 | - | Toomas Talumets v Yevhenii Cherkashyn | L | 3-1 | |
| TT Cup | 04/30 12:45 | - | Vootele Vaher v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 04/30 11:45 | - | Yevhenii Cherkashyn v Grigori Maltizov | W | 3-1 | |
| TT Cup | 04/30 10:15 | - | Toomas Talumets v Yevhenii Cherkashyn | L | 3-1 | |
| TT Cup | 04/25 13:15 | - | Yevhenii Cherkashyn v Grigori Maltizov | L | 1-3 | |
| TT Cup | 04/25 12:15 | - | Grigori Maltizov v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 04/25 11:45 | - | Yevhenii Cherkashyn v Rene Riomar | L | 1-3 | |
| TT Cup | 04/25 10:15 | - | Edvinas Tamashauskas v Yevhenii Cherkashyn | L | 3-1 | |
| TT Cup | 04/23 13:50 | - | Yevhenii Cherkashyn v Mart Martin | L | 0-3 | |
| TT Cup | 04/23 12:45 | - | Edvinas Tamashauskas v Yevhenii Cherkashyn | L | 3-1 | |
| TT Cup | 04/23 11:45 | - | Yevhenii Cherkashyn v Grigori Maltizov | W | 3-0 | |
| TT Cup | 04/23 10:15 | - | Mart Martin v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 04/22 08:50 | - | Yevhenii Cherkashyn v Rene Riomar | W | 3-2 |