| 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 | |
| TT Cup | 02/26 18:45 | - | Yevhenii Cherkashyn v Le Liu | L | 0-3 | |
| TT Cup | 02/26 17:15 | - | Mart Martin v Yevhenii Cherkashyn | L | 3-2 | |
| TT Cup | 02/26 16:45 | - | Stanislav Kruti v Yevhenii Cherkashyn | L | 3-1 | |
| TT Cup | 02/24 14:45 | - | Simo Venski v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 02/24 13:15 | - | Valerii Ignatev v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 02/24 12:45 | - | Vootele Vaher v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 02/24 11:45 | - | Yevhenii Cherkashyn v Simo Venski | L | 2-3 | |
| TT Cup | 02/21 19:45 | - | Yevhenii Cherkashyn v Oliver Ollmann | W | 3-1 | |
| TT Cup | 02/21 18:45 | - | Toivo Tuisk v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup | 02/21 17:45 | - | Yevhenii Cherkashyn v Stanislav Kruti | L | 2-3 | |
| TT Cup | 02/21 16:15 | - | Oliver Ollmann v Yevhenii Cherkashyn | W | 1-3 | |
| TT Cup | 02/14 19:45 | - | Valerii Ignatev v Yevhenii Cherkashyn | L | 3-2 | |
| TT Cup | 02/14 18:15 | - | Yevhenii Cherkashyn v Vootele Vaher | W | 3-1 | |
| TT Cup | 02/14 17:15 | - | Yevhenii Cherkashyn v Yuto Kobayashi | W | 3-1 | |
| TT Cup | 02/14 16:15 | - | Yevhenii Cherkashyn v Valerii Ignatev | L | 1-3 | |
| TT Cup (2023) | 11/07 13:45 | - | Yevhenii Cherkashyn v Mart Martin | - | Cancelled | |
| TT Cup (2023) | 11/07 12:15 | - | Jaanus Lokotar v Yevhenii Cherkashyn | - | Cancelled | |
| TT Cup (2023) | 11/07 11:45 | - | Stanislav Kruti v Yevhenii Cherkashyn | D | Cancelled | |
| TT Cup (2023) | 10/31 14:25 | - | Jaanus Lokotar v Yevhenii Cherkashyn | L | 3-0 | |
| TT Cup (2023) | 10/31 13:15 | - | Mart Martin v Yevhenii Cherkashyn | L | 3-2 | |
| TT Cup (2023) | 10/31 12:45 | - | Jaanus Lokotar v Yevhenii Cherkashyn | L | 3-0 | |
| TT Cup (2023) | 10/31 11:45 | - | Yevhenii Cherkashyn v Grigori Maltizov | L | 0-3 | |
| TT Cup (2023) | 10/27 13:50 | - | Yevhenii Cherkashyn v Mart Martin | W | 3-2 | |
| TT Cup (2023) | 10/27 12:15 | - | Mart Martin v Yevhenii Cherkashyn | W | 2-3 | |
| TT Cup (2023) | 10/27 11:45 | - | Edvinas Tamashauskas v Yevhenii Cherkashyn | W | 0-3 | |
| TT Cup (2023) | 10/27 10:45 | - | Yevhenii Cherkashyn v Grigori Maltizov | W | 3-2 |