| TT Cup (2023) | 2023/08/28 15:15 | Raul Pirson v Oliver Ollman | W | 3-2 |
| TT Cup (2023) | 2023/08/25 16:45 | Oliver Ollman v Raul Pirson | L | 3-1 |
| TT Cup (2023) | 2023/08/22 17:45 | Raul Pirson v Oliver Ollman | L | 0-3 |
| TT Cup (2023) | 2023/08/16 18:15 | Raul Pirson v Oliver Ollman | L | 0-3 |
| TT Cup (2023) | 2023/08/16 15:15 | Raul Pirson v Oliver Ollman | W | 3-0 |
| TT Cup (2023) | 2023/08/07 16:15 | Oliver Ollman v Raul Pirson | L | 3-0 |
| TT Cup (2023) | 2023/07/10 17:45 | Raul Pirson v Oliver Ollman | L | 0-3 |
| TT Cup (2023) | 2023/06/12 15:45 | Raul Pirson v Oliver Ollman | L | 1-3 |
| TT Cup (2023) | 2023/11/13 17:15 | Toivo Tuisk v Raul Pirson | W | 1-3 |
| TT Cup (2023) | 2023/11/13 16:45 | Heino Laidmaa v Raul Pirson | L | 3-2 |
| TT Cup (2023) | 2023/11/03 20:00 | Raul Pirson v Brunold Oja | W | 3-2 |
| TT Cup (2023) | 2023/11/03 18:15 | Raul Pirson v Aleksandr Sokirjanski | W | 3-2 |
| TT Cup (2023) | 2023/11/03 17:15 | Raul Pirson v Brunold Oja | W | 3-0 |
| TT Cup (2023) | 2023/11/03 16:15 | Raul Pirson v Valdek Putkemaa | W | 3-1 |
| TT Cup (2023) | 2023/11/02 10:30 | Raul Pirson v Vootele Vaher | L | 2-3 |
| TT Cup (2023) | 2023/11/02 09:15 | Raul Pirson v Vootele Vaher | L | 2-3 |
| TT Cup (2023) | 2023/11/13 17:45 | Oliver Ollman v Heino Laidmaa | W | 3-1 |
| TT Cup (2023) | 2023/11/13 16:15 | Toivo Tuisk v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/10/30 19:50 | Oliver Ollman v Madis Vaarpu | W | 3-0 |
| TT Cup (2023) | 2023/10/30 18:15 | Madis Vaarpu v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/10/30 17:45 | Konstantin Akimov v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/10/30 16:45 | Oliver Ollman v Eduard Pukkonen | W | 3-2 |
| TT Cup (2023) | 2023/10/27 18:50 | Mati Krusel v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/10/27 17:15 | Oliver Ollman v Mati Krusel | L | 1-3 |