| TT Cup | 04/22 05:45 | - | Mart Martin v Yevhenii Cherkashyn | L | 3-2 | |
| TT Cup | 04/15 18:45 | - | Vootele Vaher v Yevhenii Cherkashyn | W | 2-3 | |
| TT Cup | 04/15 17:45 | - | Voldemar Tusis v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 04/15 16:45 | - | Yevhenii Cherkashyn v Vootele Vaher | L | 0-3 | |
| TT Cup | 04/15 15:15 | - | Valerii Ignatev v Yevhenii Cherkashyn | W | 1-3 | |
| TT Cup | 03/29 10:25 | - | Yevhenii Cherkashyn v Oliver Ollmann | L | 1-3 | |
| TT Cup | 03/29 08:45 | - | Kalle Kask v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 03/29 08:15 | - | Oliver Ollmann v Yevhenii Cherkashyn | W | 1-3 | |
| TT Cup | 03/29 07:15 | - | Yevhenii Cherkashyn v Yuto Kobayashi | W | 3-1 | |
| TT Cup | 03/19 14:55 | - | Stanislav Kruti v Yevhenii Cherkashyn | L | 3-1 | |
| TT Cup | 03/19 13:45 | - | Stanislav Kruti v Yevhenii Cherkashyn | L | 3-2 | |
| TT Cup | 03/19 12:45 | - | Yevhenii Cherkashyn v Oliver Ollmann | W | 3-2 | |
| TT Cup | 03/19 11:15 | - | Johannes Kant v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 03/11 09:45 | - | Yevhenii Cherkashyn v Nikolai Danilov | W | 3-0 | |
| TT Cup | 03/11 08:45 | - | Oliver Ollmann v Yevhenii Cherkashyn | L | 3-2 | |
| TT Cup | 03/11 08:15 | - | Stanislav Kruti v Yevhenii Cherkashyn | L | 3-0 | |
| TT Cup | 03/11 07:15 | - | Yevhenii Cherkashyn v Nikolai Danilov | W | 3-0 | |
| TT Cup | 03/08 09:45 | - | Edvinas Tamashauskas v Yevhenii Cherkashyn | L | 3-0 | |
| TT Cup | 03/08 09:15 | - | Mart Martin v Yevhenii Cherkashyn | L | 3-0 | |
| TT Cup | 03/08 08:15 | - | Yevhenii Cherkashyn v Edvinas Tamashauskas | L | 2-3 | |
| TT Cup | 03/08 06:45 | - | Markus-Oliver Annuk v Yevhenii Cherkashyn | L | 3-0 | |
| TT Cup | 03/07 14:15 | - | Grigori Maltizov v Yevhenii Cherkashyn | L | 3-2 | |
| TT Cup | 03/07 13:15 | - | Yevhenii Cherkashyn v Edvinas Tamashauskas | L | 1-3 | |
| TT Cup | 03/07 12:15 | - | Yevhenii Cherkashyn v Grigori Maltizov | L | 0-3 | |
| TT Cup | 03/07 11:15 | - | Yevhenii Cherkashyn v Martin Mart | L | 1-3 | |
| TT Cup | 03/05 14:15 | - | Grigori Maltizov v Yevhenii Cherkashyn | L | 3-0 | |
| TT Cup | 03/05 13:15 | - | Andrus Steinbach v Yevhenii Cherkashyn | L | 3-2 | |
| TT Cup | 03/05 12:45 | - | Yevhenii Cherkashyn v Lauri Ulla | L | 1-3 | |
| TT Cup | 03/05 11:15 | - | Grigori Maltizov v Yevhenii Cherkashyn | L | 3-1 | |
| TT Cup | 02/26 19:15 | - | Stanislav Kruti v Yevhenii Cherkashyn | W | 0-3 |