| TT Cup (2023) | 2023/03/23 09:15 | Raul Pirson v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/03/15 10:15 | Raul Pirson v Oliver Ollman | L | 3-1 |
| TT Cup (2023) | 2023/03/15 09:15 | Oliver Ollman v Raul Pirson | L | 0-3 |
| TT Cup (2023) | 2023/03/13 08:45 | Oliver Ollman v Raul Pirson | W | 3-0 |
| TT Cup (2023) | 2023/03/06 09:15 | Raul Pirson v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/02/28 09:15 | Oliver Ollman v Raul Pirson | W | 3-0 |
| TT Cup (2023) | 2023/02/20 09:15 | Raul Pirson v Oliver Ollman | L | 3-1 |
| TT Cup (2023) | 2023/02/13 06:45 | Raul Pirson v Oliver Ollman | W | 1-3 |
| 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 |
| TT Cup (2023) | 2023/03/29 09:15 | Stanislav Kruti v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/03/29 07:45 | Vincent Oberle v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/03/29 07:15 | Martin Pakk v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/03/29 06:15 | Oliver Ollman v Stanislav Kruti | L | 2-3 |
| 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) | 2023/04/05 13:45 | Ermo Veelain v Raul Pirson | L | 3-2 |
| TT Cup (2023) | 2023/04/05 12:15 | Madis Vaarpu v Raul Pirson | W | 1-3 |
| TT Cup (2023) | 2023/04/05 11:45 | Mart Ojamaa v Raul Pirson | W | 0-3 |
| TT Cup (2023) | 2023/04/05 10:45 | Raul Pirson v Ermo Veelain | L | 1-3 |