| TT Cup (2023) | 2023/01/09 10:15 | Oliver Ollman v Raul Pirson | L | 1-3 |
| TT Cup (2023) | 2023/01/09 07:45 | Raul Pirson v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/01/04 09:45 | Oliver Ollman v Raul Pirson | W | 3-1 |
| TT Cup (2023) | 2023/01/04 09:15 | Raul Pirson v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/01/03 12:45 | Raul Pirson v Oliver Ollman | L | 3-2 |
| TT Cup (2022) | 2022/12/20 06:45 | Raul Pirson v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/01/21 12:15 | Meelis Kreegi v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/01/21 11:45 | Timo Siim v Oliver Ollman | L | 3-1 |
| TT Cup (2023) | 2023/01/17 10:15 | Oliver Ollman v Elvis Libene | W | 3-0 |
| TT Cup (2023) | 2023/01/17 09:15 | Elvis Libene v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/01/17 08:15 | Oliver Ollman v Oleg Gussarov | W | 3-0 |
| TT Cup (2023) | 2023/01/17 06:45 | Yuto Kobayashi v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/01/10 14:45 | Oleg Jefremov v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/01/10 13:45 | Oliver Ollman v Oleg Jefremov | L | 0-3 |
| TT Cup (2023) | 2023/01/21 12:45 | Raul Pirson v Meelis Kreegi | W | 3-1 |
| TT Cup (2023) | 2023/01/21 11:15 | Timo Siim v Raul Pirson | L | 3-1 |
| TT Cup (2023) | 2023/01/18 14:15 | Raul Pirson v Heldur Nermann | W | 3-1 |
| TT Cup (2023) | 2023/01/18 13:45 | Ermo Veelain v Raul Pirson | L | 3-1 |
| TT Cup (2023) | 2023/01/18 12:45 | Raul Pirson v Yuto Kobayashi | L | 1-3 |
| TT Cup (2023) | 2023/01/18 11:15 | Heldur Nermann v Raul Pirson | W | 2-3 |
| TT Cup (2023) | 2023/01/16 14:45 | Raul Pirson v Yuto Kobayashi | L | 1-3 |
| TT Cup (2023) | 2023/01/16 13:15 | Yuto Kobayashi v Raul Pirson | W | 1-3 |