| TT Cup (2023) | 2023/07/01 10:45 | Yuto Kobayashi v Oliver Ollman | W | 3-2 |
| TT Cup (2023) | 2023/06/28 15:15 | Oliver Ollman v Yuto Kobayashi | W | 2-3 |
| TT Cup (2023) | 2023/05/12 10:15 | Oliver Ollman v Yuto Kobayashi | L | 3-1 |
| TT Cup (2023) | 2023/01/24 10:15 | Yuto Kobayashi v Oliver Ollman | L | 2-3 |
| TT Cup (2023) | 2023/01/24 08:45 | Oliver Ollman v Yuto Kobayashi | W | 1-3 |
| TT Cup (2023) | 2023/01/17 06:45 | Yuto Kobayashi v Oliver Ollman | L | 2-3 |
| TT Cup (2023) | 2023/01/09 09:15 | Oliver Ollman v Yuto Kobayashi | L | 3-2 |
| TT Cup (2023) | 2023/07/01 12:15 | Stanislav Kruti v Yuto Kobayashi | L | 3-1 |
| TT Cup (2023) | 2023/07/01 11:45 | Meelis Apsolon v Yuto Kobayashi | L | 3-2 |
| TT Cup (2023) | 2023/07/01 10:45 | Yuto Kobayashi v Oliver Ollman | W | 3-2 |
| TT Cup (2023) | 2023/06/28 18:15 | Yuto Kobayashi v Enno Vinne | W | 3-1 |
| TT Cup (2023) | 2023/06/28 17:45 | Enno Vinne v Yuto Kobayashi | W | 0-3 |
| TT Cup (2023) | 2023/06/28 16:45 | Yuto Kobayashi v Toivo Tuisk | L | 1-3 |
| TT Cup (2023) | 2023/06/28 15:15 | Oliver Ollman v Yuto Kobayashi | W | 2-3 |
| TT Cup (2023) | 2023/06/13 08:45 | Yuto Kobayashi v Koit Karjus | W | 3-1 |
| TT Cup (2023) | 2023/07/01 12:45 | Oliver Ollman v Meelis Apsolon | L | 2-3 |
| TT Cup (2023) | 2023/07/01 11:15 | Stanislav Kruti v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/07/01 10:45 | Yuto Kobayashi v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/06/28 18:45 | Toivo Tuisk v Oliver Ollman | L | 3-1 |
| TT Cup (2023) | 2023/06/28 17:15 | Oliver Ollman v Toivo Tuisk | W | 3-2 |
| TT Cup (2023) | 2023/06/28 16:15 | Oliver Ollman v Enno Vinne | W | 3-1 |
| TT Cup (2023) | 2023/06/28 15:15 | Oliver Ollman v Yuto Kobayashi | L | 2-3 |
| TT Cup (2023) | 2023/06/12 18:45 | Oliver Ollman v Enno Vinne | W | 3-1 |