| TT Cup (2023) | 2023/06/12 15:45 | Raul Pirson v Oliver Ollman | L | 1-3 |
| 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) | 2023/07/10 16:15 | Toivo Tuisk v Raul Pirson | L | 3-2 |
| TT Cup (2023) | 2023/07/10 15:45 | Aleksandr Sokirjanski v Raul Pirson | W | 0-3 |
| TT Cup (2023) | 2023/07/04 18:45 | Vadim Strogov v Raul Pirson | W | 0-3 |
| TT Cup (2023) | 2023/07/04 17:45 | Enno Vinne v Raul Pirson | W | 1-3 |
| TT Cup (2023) | 2023/07/04 16:45 | Raul Pirson v Heino Laidmaa | W | 3-1 |
| TT Cup (2023) | 2023/07/04 15:15 | Vadim Strogov v Raul Pirson | L | 3-1 |
| TT Cup (2023) | 2023/06/30 13:15 | Raul Pirson v Heldur Nermann | W | 3-2 |
| TT Cup (2023) | 2023/06/30 12:45 | Raul Pirson v Koit Karjus | L | 0-3 |
| TT Cup (2023) | 2023/07/10 16:45 | Oliver Ollman v Aleksandr Sokirjanski | W | 3-0 |
| TT Cup (2023) | 2023/07/10 15:15 | Toivo Tuisk v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/07/01 13:15 | Yuto Kobayashi v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/07/01 12:45 | Oliver Ollman v Meelis Apsolon | L | 2-3 |
| TT Cup (2023) | 2023/07/01 11:15 | Stanislav Kruti v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/07/01 10:45 | Yuto Kobayashi v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/06/28 18:45 | Toivo Tuisk v Oliver Ollman | L | 3-1 |
| TT Cup (2023) | 2023/06/28 17:15 | Oliver Ollman v Toivo Tuisk | W | 3-2 |