| TT Cup (2023) | 2023/08/16 15:15 | Raul Pirson v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/08/07 18:45 | Mart Martin v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/08/07 17:15 | Oliver Ollman v Mart Martin | L | 2-3 |
| TT Cup (2023) | 2023/08/07 16:15 | Oliver Ollman v Raul Pirson | W | 3-0 |
| TT Cup (2023) | 2023/08/07 15:15 | Oliver Ollman v Toivo Tuisk | W | 3-0 |
| TT Cup (2023) | 2023/07/26 18:15 | Oliver Ollman v Toivo Tuisk | W | 3-1 |
| TT Cup (2023) | 2023/07/26 17:45 | Toivo Tuisk v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/07/26 16:45 | Oliver Ollman v Gerrit Hallmagi | L | 2-3 |
| TT Cup (2023) | 2023/08/16 15:45 | Heino Laidmaa v Mart Martin | L | 0-3 |
| TT Cup (2023) | 2023/08/15 13:15 | Heino Laidmaa v Mart Ojamaa | L | 1-3 |
| TT Cup (2023) | 2023/08/15 12:45 | Madis Vaarpu v Heino Laidmaa | W | 2-3 |
| TT Cup (2023) | 2023/08/15 11:45 | Heino Laidmaa v Mart Ojamaa | W | 3-0 |
| TT Cup (2023) | 2023/08/15 10:15 | Johannes Kant v Heino Laidmaa | L | 3-1 |
| TT Cup (2023) | 2023/08/10 18:45 | Brunold Oja v Heino Laidmaa | L | 3-1 |
| TT Cup (2023) | 2023/08/10 17:15 | Heino Laidmaa v Brunold Oja | L | 1-3 |
| TT Cup (2023) | 2023/08/10 16:15 | Heino Laidmaa v Aleksandr Sokirjanski | W | 3-1 |