Stadium: Estonia 3
| TT Cup | 2024/03/29 10:25 | Yevhenii Cherkashyn v Oliver Ollman | W | 1-3 |
| TT Cup | 2024/03/29 08:15 | Oliver Ollman v Yevhenii Cherkashyn | L | 1-3 |
| TT Cup | 2024/03/19 12:45 | Yevhenii Cherkashyn v Oliver Ollman | L | 3-2 |
| TT Cup | 2024/03/11 08:45 | Oliver Ollman v Yevhenii Cherkashyn | W | 3-2 |
| TT Cup | 2024/02/21 19:45 | Yevhenii Cherkashyn v Oliver Ollman | L | 3-1 |
| TT Cup | 2024/02/21 16:15 | Oliver Ollman v Yevhenii Cherkashyn | L | 1-3 |
| TT Cup | 2024/05/24 16:15 | Oliver Ollman v Stanislav Kruti | W | 3-0 |
| TT Cup | 2024/05/24 15:15 | Oliver Ollman v Toivo Tuisk | W | 3-1 |
| TT Cup | 2024/05/09 18:55 | Oliver Ollman v Taimo Jullinen | W | 3-2 |
| TT Cup | 2024/05/09 17:15 | Oliver Ollman v Voldemar Tusis | W | 3-2 |
| TT Cup | 2024/05/09 16:15 | Oliver Ollman v Taimo Jullinen | W | 3-1 |
| TT Cup | 2024/05/09 15:20 | Oliver Ollman v Stanislav Kruti | W | 3-0 |
| TT Cup | 2024/05/01 18:45 | Stanislav Kruti v Oliver Ollman | L | 3-1 |
| TT Cup | 2024/05/01 17:45 | Meelis Apsolon v Oliver Ollman | W | 0-3 |
| TT Cup | 2024/05/24 16:45 | Toivo Tuisk v Yevhenii Cherkashyn | W | 0-3 |
| TT Cup | 2024/05/24 15:45 | Yevhenii Cherkashyn v Stanislav Kruti | W | 3-1 |
| TT Cup | 2024/05/02 13:15 | Vootele Vaher v Yevhenii Cherkashyn | L | 3-1 |
| TT Cup | 2024/05/02 12:45 | Yevhenii Cherkashyn v Vootele Vaher | L | 0-3 |
| TT Cup | 2024/05/02 11:15 | Jaanus Lokotar v Yevhenii Cherkashyn | W | 1-3 |
| TT Cup | 2024/05/02 10:45 | Rene Riomar v Yevhenii Cherkashyn | L | 3-2 |
| TT Cup | 2024/04/30 13:50 | Toomas Talumets v Yevhenii Cherkashyn | L | 3-1 |
| TT Cup | 2024/04/30 12:45 | Vootele Vaher v Yevhenii Cherkashyn | W | 0-3 |