| TT Cup | 2023/07/01 13:15 | Yuto Kobayashi v Oliver Ollman | W | 3-2 |
| TT Cup | 2023/07/01 10:45 | Yuto Kobayashi v Oliver Ollman | W | 3-2 |
| TT Cup | 2023/06/28 15:15 | Oliver Ollman v Yuto Kobayashi | W | 2-3 |
| TT Cup | 2023/05/12 10:15 | Oliver Ollman v Yuto Kobayashi | L | 3-1 |
| TT Cup | 2023/01/24 10:15 | Yuto Kobayashi v Oliver Ollman | L | 2-3 |
| TT Cup | 2023/01/24 08:45 | Oliver Ollman v Yuto Kobayashi | W | 1-3 |
| TT Cup | 2023/01/17 06:45 | Yuto Kobayashi v Oliver Ollman | L | 2-3 |
| TT Cup | 2023/01/09 09:15 | Oliver Ollman v Yuto Kobayashi | L | 3-2 |
| TT Cup | 2023/07/19 08:45 | Meelis Apsolon v Yuto Kobayashi | W | 1-3 |
| TT Cup | 2023/07/19 07:45 | Yuto Kobayashi v Meelis Apsolon | L | 0-3 |
| TT Cup | 2023/07/19 06:45 | Yuto Kobayashi v Rene Riomar | L | 0-3 |
| TT Cup | 2023/07/19 05:45 | Yuto Kobayashi v Stanislav Fjodorov | L | 2-3 |
| TT Cup | 2023/07/12 09:15 | Aleksandr Dulov v Yuto Kobayashi | L | 3-1 |
| TT Cup | 2023/07/12 07:45 | Yuto Kobayashi v Kalle Kask | W | 3-1 |
| TT Cup | 2023/07/12 06:45 | Yuto Kobayashi v Aleksandr Dulov | L | 1-3 |
| TT Cup | 2023/07/12 05:45 | Yuto Kobayashi v Martin Pakk | W | 3-0 |
| TT Cup | 2023/07/10 18:45 | Oliver Ollman v Toivo Tuisk | L | 2-3 |
| TT Cup | 2023/07/10 17:45 | Raul Pirson v Oliver Ollman | W | 0-3 |
| TT Cup | 2023/07/10 16:45 | Oliver Ollman v Aleksandr Sokirjanski | W | 3-0 |
| TT Cup | 2023/07/10 15:15 | Toivo Tuisk v Oliver Ollman | W | 2-3 |
| TT Cup | 2023/07/01 13:15 | Yuto Kobayashi v Oliver Ollman | L | 3-2 |
| TT Cup | 2023/07/01 12:45 | Oliver Ollman v Meelis Apsolon | L | 2-3 |
| TT Cup | 2023/07/01 11:15 | Stanislav Kruti v Oliver Ollman | L | 3-0 |
| TT Cup | 2023/07/01 10:45 | Yuto Kobayashi v Oliver Ollman | L | 3-2 |