| TT Cup (2023) | 2023/10/06 15:15 | Heino Laidmaa v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/08/28 18:15 | Heino Laidmaa v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/08/28 17:45 | Heino Laidmaa v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/08/16 16:45 | Oliver Ollman v Heino Laidmaa | W | 3-1 |
| TT Cup (2023) | 2023/10/13 15:15 | Dmitry Fomichenko v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/10/09 18:45 | Oliver Ollman v Valdek Putkemaa | W | 3-1 |
| TT Cup (2023) | 2023/10/09 17:45 | Konstantin Akimov v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/10/09 16:45 | 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) | 2023/10/13 15:45 | Heino Laidmaa v Toivo Tuisk | L | 0-3 |
| TT Cup (2023) | 2023/10/06 18:20 | Heino Laidmaa v Dmitry Fomichenko | L | 0-3 |
| TT Cup (2023) | 2023/10/06 17:15 | Heino Laidmaa v Dmitry Fomichenko | W | 3-1 |
| TT Cup (2023) | 2023/10/06 16:15 | Heino Laidmaa v Valdek Putkemaa | L | 1-3 |
| TT Cup (2023) | 2023/10/06 15:15 | Heino Laidmaa v Oliver Ollman | L | 2-3 |
| TT Cup (2023) | 2023/09/21 18:15 | Heino Laidmaa v Brunold Oja | W | 3-0 |
| TT Cup (2023) | 2023/09/21 17:15 | Heino Laidmaa v Yuto Kobayashi | L | 1-3 |
| TT Cup (2023) | 2023/09/21 16:15 | Heino Laidmaa v Toivo Tuisk | L | 2-3 |