| TT Cup (2023) | 2023/10/13 16:45 | Oliver Ollman v Heino Laidmaa | W | 3-2 |
| 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) | 2023/10/27 15:15 | Oliver Ollman v Valdek Putkemaa | W | 3-1 |
| TT Cup (2023) | 2023/10/19 18:55 | Oliver Ollman v Aleksandr Sokirjanski | L | 2-3 |
| TT Cup (2023) | 2023/10/19 17:15 | Aleksandr Sokirjanski v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/10/19 16:45 | Dmitry Fomichenko v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/10/19 15:45 | Oliver Ollman v Toivo Tuisk | W | 3-2 |
| TT Cup (2023) | 2023/10/13 18:50 | Dmitry Fomichenko v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/10/13 17:45 | Toivo Tuisk v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/10/13 16:45 | Oliver Ollman v Heino Laidmaa | W | 3-2 |
| TT Cup (2023) | 2023/10/27 15:45 | Mati Krusel v Heino Laidmaa | L | 3-0 |
| TT Cup (2023) | 2023/10/13 18:20 | Toivo Tuisk v Heino Laidmaa | W | 2-3 |
| TT Cup (2023) | 2023/10/13 17:15 | Dmitry Fomichenko v Heino Laidmaa | W | 1-3 |
| TT Cup (2023) | 2023/10/13 16:45 | Oliver Ollman v Heino Laidmaa | L | 3-2 |
| 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 |