| 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 | |
| TT Cup | 04/22 07:45 | - | Edvinas Tamashauskas v Yevhenii Cherkashyn | L | 3-2 | |
| TT Cup | 04/22 07:15 | - | Yevhenii Cherkashyn v Rene Riomar | W | 3-1 | |
| 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 |