| TT Cup (2023) | 2023/07/10 17:45 | Raul Pirson 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 15:45 | Oliver Ollman v Raul Pirson | W | 3-1 |
| TT Cup (2023) | 2023/03/23 09:15 | Raul Pirson v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/03/15 10:15 | Raul Pirson v Oliver Ollman | L | 3-1 |
| TT Cup (2023) | 2023/03/15 09:15 | Oliver Ollman v Raul Pirson | L | 0-3 |
| TT Cup (2023) | 2023/03/13 08:45 | Oliver Ollman v Raul Pirson | W | 3-0 |
| TT Cup (2023) | 2023/03/06 09:15 | Raul Pirson v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/08/07 15:15 | Oliver Ollman v Toivo Tuisk | W | 3-0 |
| TT Cup (2023) | 2023/07/26 18:15 | Oliver Ollman v Toivo Tuisk | W | 3-1 |
| TT Cup (2023) | 2023/07/26 17:45 | Toivo Tuisk v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/07/26 16:45 | Oliver Ollman v Gerrit Hallmagi | L | 2-3 |
| TT Cup (2023) | 2023/07/26 15:15 | Yuto Kobayashi v Oliver Ollman | L | 3-1 |
| TT Cup (2023) | 2023/07/10 18:45 | Oliver Ollman v Toivo Tuisk | L | 2-3 |
| TT Cup (2023) | 2023/07/10 17:45 | Raul Pirson v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/07/10 16:45 | Oliver Ollman v Aleksandr Sokirjanski | W | 3-0 |
| TT Cup (2023) | 2023/08/07 15:45 | Mart Martin v Raul Pirson | L | 3-0 |
| TT Cup (2023) | 2023/08/02 09:15 | Raul Pirson v Kalle Kask | W | 3-2 |
| TT Cup (2023) | 2023/08/02 08:15 | Raul Pirson v Mart Ojamaa | W | 3-1 |
| TT Cup (2023) | 2023/08/02 06:45 | Kalle Kask v Raul Pirson | W | 1-3 |
| TT Cup (2023) | 2023/08/02 06:15 | Valdek Putkemaa v Raul Pirson | W | 0-3 |
| TT Cup (2023) | 2023/07/20 18:45 | Raul Pirson v Dmitry Fomichenko | W | 3-2 |
| TT Cup (2023) | 2023/07/20 17:15 | Raul Pirson v Brunold Oja | W | 3-1 |
| TT Cup (2023) | 2023/07/20 16:15 | Raul Pirson v Dmitry Fomichenko | W | 3-2 |