| TT Cup (2023) | 2023/02/07 08:45 | Oliver Ollman v Stanislav Kruti | L | 1-3 |
| TT Cup (2023) | 2023/03/23 10:15 | Oliver Ollman v Vincent Oberle | L | 0-3 |
| TT Cup (2023) | 2023/03/23 09:15 | Raul Pirson v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/03/23 08:15 | Oliver Ollman v Mart Ojamaa | W | 3-1 |
| TT Cup (2023) | 2023/03/23 06:45 | Vincent Oberle v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/03/15 10:15 | Raul Pirson v Oliver Ollman | L | 3-1 |
| TT Cup (2023) | 2023/03/15 09:15 | Oliver Ollman v Raul Pirson | L | 0-3 |
| TT Cup (2023) | 2023/03/15 07:45 | Heldur Nermann v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/03/15 07:15 | Ermo Veelain v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/03/24 19:15 | Stanislav Kruti v Arvi Tammoja | L | 0-3 |
| TT Cup (2023) | 2023/03/24 18:15 | Stanislav Kruti v Anton Kukeste | L | 1-3 |
| TT Cup (2023) | 2023/03/24 17:15 | Stanislav Kruti v Viljar Laidvee | L | 1-3 |
| TT Cup (2023) | 2023/03/24 16:15 | Stanislav Kruti v Arvi Tammoja | W | 3-2 |
| TT Cup (2023) | 2023/03/22 14:15 | Stanislav Kruti v Martin Pakk | W | 3-0 |
| TT Cup (2023) | 2023/03/22 13:15 | Martin Pakk v Stanislav Kruti | W | 0-3 |
| TT Cup (2023) | 2023/03/22 12:45 | Arvi Tammoja v Stanislav Kruti | L | 3-0 |
| TT Cup (2023) | 2023/03/22 11:45 | Stanislav Kruti v Aleksandr Dulov | L | 2-3 |