| 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 (2023) | 2023/06/28 15:15 | Oliver Ollman v Yuto Kobayashi | L | 2-3 |
| TT Cup (2023) | 2023/05/12 10:15 | Oliver Ollman v Yuto Kobayashi | W | 3-1 |
| TT Cup (2023) | 2023/12/13 14:30 | Oliver Ollman v Jaanus Lokotar | L | 1-3 |
| TT Cup (2023) | 2023/12/13 13:45 | Jaanus Lokotar v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/12/13 12:45 | Oliver Ollman v Mart Martin | L | 0-3 |
| TT Cup (2023) | 2023/12/13 11:15 | Stanislav Kruti v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/12/11 19:55 | Oliver Ollman v Toivo Tuisk | W | 3-0 |
| TT Cup (2023) | 2023/12/11 18:45 | Toivo Tuisk v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/12/11 17:45 | Oliver Ollman v Nikolai Danilov | W | 3-0 |
| TT Cup (2023) | 2023/12/11 16:15 | Valdek Putkemaa v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/12/20 19:25 | Valerii Ignatev v Yuto Kobayashi | L | 3-2 |
| TT Cup (2023) | 2023/12/20 18:15 | Mart Martin v Yuto Kobayashi | L | 3-0 |
| TT Cup (2023) | 2023/12/20 17:45 | Vootele Vaher v Yuto Kobayashi | L | 3-1 |
| TT Cup (2023) | 2023/12/20 16:45 | Yuto Kobayashi v Valerii Ignatev | L | 0-3 |
| TT Cup (2023) | 2023/12/07 10:25 | Edvinas Tamashauskas v Yuto Kobayashi | W | 0-3 |
| TT Cup (2023) | 2023/12/07 08:45 | Oliver Ollman v Yuto Kobayashi | W | 1-3 |
| TT Cup (2023) | 2023/12/07 08:15 | Edvinas Tamashauskas v Yuto Kobayashi | L | 3-1 |
| TT Cup (2023) | 2023/12/07 07:15 | Yuto Kobayashi v Vootele Vaher | W | 3-1 |