| TT Cup (2023) | 2023/06/01 15:45 | Oliver Ollman v Raul Pirson | L | 3-1 |
| TT Cup (2023) | 2023/03/23 09:15 | Raul Pirson v Oliver Ollman | L | 0-3 |
| TT Cup (2023) | 2023/03/15 10:15 | Raul Pirson v Oliver Ollman | W | 3-1 |
| TT Cup (2023) | 2023/03/15 09:15 | Oliver Ollman v Raul Pirson | W | 0-3 |
| TT Cup (2023) | 2023/03/13 08:45 | Oliver Ollman v Raul Pirson | L | 3-0 |
| TT Cup (2023) | 2023/03/06 09:15 | Raul Pirson v Oliver Ollman | L | 1-3 |
| TT Cup (2023) | 2023/02/28 09:15 | Oliver Ollman v Raul Pirson | L | 3-0 |
| TT Cup (2023) | 2023/02/20 09:15 | Raul Pirson v Oliver Ollman | W | 3-1 |
| TT Cup (2023) | 2023/06/01 18:15 | Toivo Tuisk v Raul Pirson | L | 3-1 |
| TT Cup (2023) | 2023/06/01 17:45 | Raul Pirson v Toivo Tuisk | L | 0-3 |
| TT Cup (2023) | 2023/06/01 16:15 | Vootele Vaher v Raul Pirson | L | 3-1 |
| TT Cup (2023) | 2023/06/01 15:45 | Oliver Ollman v Raul Pirson | L | 3-1 |
| TT Cup (2023) | 2023/05/03 09:15 | Martin Pakk v Raul Pirson | L | 3-2 |
| TT Cup (2023) | 2023/05/03 07:45 | Raul Pirson v Oleg Gussarov | W | 3-0 |
| TT Cup (2023) | 2023/05/03 06:45 | Raul Pirson v Mart Ojamaa | W | 3-0 |
| TT Cup (2023) | 2023/05/03 05:45 | Raul Pirson v Martin Pakk | L | 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) | 2023/05/12 13:45 | Dmitri Donskov v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/05/12 12:15 | Oliver Ollman v Valdek Putkemaa | W | 3-1 |
| TT Cup (2023) | 2023/05/12 11:15 | Oliver Ollman v Dmitri Donskov | L | 0-3 |
| TT Cup (2023) | 2023/05/12 10:15 | Oliver Ollman v Yuto Kobayashi | W | 3-1 |