| TT Cup (2023) | 2023/05/12 10:15 | Oliver Ollman v Yuto Kobayashi | W | 3-1 |
| TT Cup (2023) | 2023/01/24 10:15 | Yuto Kobayashi v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/01/24 08:45 | Oliver Ollman v Yuto Kobayashi | L | 1-3 |
| TT Cup (2023) | 2023/01/17 06:45 | Yuto Kobayashi v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/01/09 09:15 | Oliver Ollman v Yuto Kobayashi | W | 3-2 |
| TT Cup (2023) | 2023/06/12 18:45 | Oliver Ollman v Enno Vinne | W | 3-1 |
| TT Cup (2023) | 2023/06/12 17:45 | Oliver Ollman v Oleg Gussarov | W | 3-0 |
| TT Cup (2023) | 2023/06/12 16:15 | Enno Vinne v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/06/12 15:45 | Raul Pirson v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/06/01 18:45 | Vootele Vaher v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/06/01 17:15 | Vootele Vaher v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/06/01 16:45 | Toivo Tuisk v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/06/01 15:45 | Oliver Ollman v Raul Pirson | W | 3-1 |
| TT Cup (2023) | 2023/06/13 08:45 | Yuto Kobayashi v Koit Karjus | W | 3-1 |
| TT Cup (2023) | 2023/06/13 08:15 | Martin Pakk v Yuto Kobayashi | L | 3-1 |
| TT Cup (2023) | 2023/06/13 07:15 | Yuto Kobayashi v Koit Karjus | W | 3-1 |
| TT Cup (2023) | 2023/06/13 05:45 | Vincent Oberle v Yuto Kobayashi | L | 3-1 |
| TT Cup (2023) | 2023/06/03 13:45 | Stanislav Kruti v Yuto Kobayashi | L | 3-1 |
| TT Cup (2023) | 2023/06/03 12:45 | Yuto Kobayashi v Meelis Apsolon | W | 3-2 |
| TT Cup (2023) | 2023/06/03 11:15 | Martin Salong v Yuto Kobayashi | W | 0-3 |
| TT Cup (2023) | 2023/06/03 10:45 | Stanislav Kruti v Yuto Kobayashi | L | 3-1 |