| TT Cup (2023) | 2023/12/22 14:45 | Yuto Kobayashi v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/12/22 11:15 | Oliver Ollman v Yuto Kobayashi | L | 2-3 |
| TT Cup (2023) | 2023/12/07 08:45 | Oliver Ollman v Yuto Kobayashi | L | 1-3 |
| TT Cup (2023) | 2023/12/05 10:25 | Oliver Ollman v Yuto Kobayashi | L | 2-3 |
| TT Cup (2023) | 2023/12/05 07:15 | Oliver Ollman v Yuto Kobayashi | W | 3-1 |
| TT Cup (2023) | 2023/07/26 15:15 | Yuto Kobayashi v Oliver Ollman | L | 3-1 |
| TT Cup (2023) | 2023/07/01 13:15 | Yuto Kobayashi v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/07/01 10:45 | Yuto Kobayashi v Oliver Ollman | L | 3-2 |
| TT Cup | 2024/01/11 11:15 | Andrus Steinbach v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/12/27 14:25 | Oliver Ollman v Stanislav Kruti | W | 3-1 |
| TT Cup (2023) | 2023/12/27 13:15 | Oliver Ollman v Andrus Steinbach | L | 0-3 |
| TT Cup (2023) | 2023/12/27 12:15 | Oliver Ollman v Stanislav Kruti | W | 3-1 |
| TT Cup (2023) | 2023/12/27 11:15 | Oliver Ollman v Mart Martin | L | 0-3 |
| TT Cup (2023) | 2023/12/26 14:55 | Oliver Ollman v Mart Martin | L | 0-3 |
| TT Cup (2023) | 2023/12/26 13:15 | Mart Martin v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/12/26 12:45 | Jaanus Lokotar v Oliver Ollman | W | 1-3 |
| TT Cup | 2024/01/11 11:45 | Yuto Kobayashi v Gerrit Hallmagi | W | 3-1 |
| TT Cup | 2024/01/04 14:15 | Andrus Steinbach v Yuto Kobayashi | W | 1-3 |
| TT Cup | 2024/01/04 13:45 | Andrus Steinbach v Yuto Kobayashi | L | 3-0 |
| TT Cup | 2024/01/04 12:45 | Yuto Kobayashi v Edvinas Tamashauskas | W | 3-2 |
| TT Cup | 2024/01/04 11:15 | Mart Martin v Yuto Kobayashi | L | 3-0 |
| TT Cup (2023) | 2023/12/22 14:45 | Yuto Kobayashi v Oliver Ollman | L | 0-3 |
| TT Cup (2023) | 2023/12/22 13:45 | Martin Pakk v Yuto Kobayashi | W | 0-3 |
| TT Cup (2023) | 2023/12/22 12:45 | Yuto Kobayashi v Jevgeni Sikorski | W | 3-1 |