| TT Cup (2023) | 2023/09/29 16:15 | Oliver Ollman v Brunold Oja | W | 3-0 |
| TT Cup (2023) | 2023/10/09 15:15 | Valdek Putkemaa v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/10/06 18:50 | Oliver Ollman v Valdek Putkemaa | L | 1-3 |
| TT Cup (2023) | 2023/10/06 17:45 | Valdek Putkemaa v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/10/06 16:45 | Oliver Ollman v Dmitry Fomichenko | L | 2-3 |
| TT Cup (2023) | 2023/10/06 15:15 | Heino Laidmaa v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/09/29 18:45 | Oliver Ollman v Valdek Putkemaa | L | 1-3 |
| TT Cup (2023) | 2023/09/29 17:15 | Oliver Ollman v Aleksandr Sokirjanski | W | 3-1 |
| TT Cup (2023) | 2023/09/29 16:15 | Oliver Ollman v Brunold Oja | W | 3-0 |
| TT Cup (2023) | 2023/10/09 15:45 | Brunold Oja v Konstantin Akimov | L | 2-3 |
| TT Cup (2023) | 2023/09/29 18:15 | Aleksandr Sokirjanski v Brunold Oja | L | 3-1 |
| TT Cup (2023) | 2023/09/29 17:45 | Brunold Oja v Valdek Putkemaa | L | 0-3 |
| TT Cup (2023) | 2023/09/29 16:15 | Oliver Ollman v Brunold Oja | L | 3-0 |
| TT Cup (2023) | 2023/09/29 15:45 | Aleksandr Sokirjanski v Brunold Oja | W | 1-3 |
| TT Cup (2023) | 2023/09/21 18:15 | Heino Laidmaa v Brunold Oja | L | 3-0 |
| TT Cup (2023) | 2023/09/21 17:45 | Toivo Tuisk v Brunold Oja | L | 3-0 |
| TT Cup (2023) | 2023/09/21 16:45 | Brunold Oja v Yuto Kobayashi | L | 0-3 |