| TT Cup (2023) | 2023/08/28 18:15 | Heino Laidmaa v Oliver Ollman | W | 3-2 |
| TT Cup (2023) | 2023/08/28 17:45 | Heino Laidmaa v Oliver Ollman | W | 3-0 |
| TT Cup (2023) | 2023/08/16 16:45 | Oliver Ollman v Heino Laidmaa | L | 3-1 |
| 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 |
| TT Cup (2023) | 2023/09/21 15:15 | Heino Laidmaa v Brunold Oja | W | 3-1 |
| TT Cup (2023) | 2023/09/15 18:45 | Heino Laidmaa v Mart Martin | W | 3-0 |
| TT Cup (2023) | 2023/09/15 17:45 | Mart Martin v Heino Laidmaa | W | 2-3 |
| TT Cup (2023) | 2023/09/15 16:45 | Heino Laidmaa v Brunold Oja | W | 3-0 |
| TT Cup (2023) | 2023/09/15 15:15 | Raul Pirson v Heino Laidmaa | W | 1-3 |
| 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) | 2023/09/29 15:15 | Oliver Ollman v Valdek Putkemaa | W | 3-0 |
| 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) | 2023/08/28 16:45 | Oliver Ollman v Vootele Vaher | L | 0-3 |
| TT Cup (2023) | 2023/08/28 15:15 | Raul Pirson v Oliver Ollman | L | 3-2 |