| TT Cup | 2023/08/07 16:15 | Oliver Ollman v Raul Pirson | L | 3-0 |
| TT Cup | 2023/07/10 17:45 | Raul Pirson v Oliver Ollman | L | 0-3 |
| TT Cup | 2023/06/12 15:45 | Raul Pirson v Oliver Ollman | L | 1-3 |
| TT Cup | 2023/06/01 15:45 | Oliver Ollman v Raul Pirson | L | 3-1 |
| TT Cup | 2023/03/23 09:15 | Raul Pirson v Oliver Ollman | L | 0-3 |
| TT Cup | 2023/03/15 10:15 | Raul Pirson v Oliver Ollman | W | 3-1 |
| TT Cup | 2023/03/15 09:15 | Oliver Ollman v Raul Pirson | W | 0-3 |
| TT Cup | 2023/03/13 08:45 | Oliver Ollman v Raul Pirson | L | 3-0 |
| TT Cup | 2023/08/11 13:45 | Johannes Kant v Raul Pirson | L | 3-2 |
| TT Cup | 2023/08/11 12:45 | Johannes Kant v Raul Pirson | L | 3-1 |
| TT Cup | 2023/08/11 11:45 | Raul Pirson v Valdek Putkemaa | W | 3-0 |
| TT Cup | 2023/08/11 10:15 | Mart Ojamaa v Raul Pirson | W | 0-3 |
| TT Cup | 2023/08/07 18:15 | Toivo Tuisk v Raul Pirson | W | 2-3 |
| TT Cup | 2023/08/07 17:45 | Raul Pirson v Toivo Tuisk | L | 1-3 |
| TT Cup | 2023/08/07 16:15 | Oliver Ollman v Raul Pirson | L | 3-0 |
| TT Cup | 2023/08/07 15:45 | Mart Martin v Raul Pirson | L | 3-0 |
| TT Cup | 2023/08/07 18:45 | Mart Martin v Oliver Ollman | W | 1-3 |
| TT Cup | 2023/08/07 17:15 | Oliver Ollman v Mart Martin | L | 2-3 |
| TT Cup | 2023/08/07 16:15 | Oliver Ollman v Raul Pirson | W | 3-0 |
| TT Cup | 2023/08/07 15:15 | Oliver Ollman v Toivo Tuisk | W | 3-0 |
| TT Cup | 2023/07/26 18:15 | Oliver Ollman v Toivo Tuisk | W | 3-1 |
| TT Cup | 2023/07/26 17:45 | Toivo Tuisk v Oliver Ollman | W | 2-3 |
| TT Cup | 2023/07/26 16:45 | Oliver Ollman v Gerrit Hallmagi | L | 2-3 |
| TT Cup | 2023/07/26 15:15 | Yuto Kobayashi v Oliver Ollman | L | 3-1 |