| 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) | 2023/08/28 17:45 | Heino Laidmaa v Oliver Ollman | W | 3-0 |
| TT Cup (2023) | 2023/08/28 16:15 | Raul Pirson v Heino Laidmaa | L | 3-2 |
| TT Cup (2023) | 2023/08/28 15:45 | Vootele Vaher v Heino Laidmaa | L | 3-1 |
| TT Cup (2023) | 2023/08/24 13:45 | Heino Laidmaa v Koit Karjus | W | 3-0 |
| TT Cup (2023) | 2023/08/24 12:45 | Madis Vaarpu v Heino Laidmaa | W | 1-3 |
| TT Cup (2023) | 2023/08/24 11:45 | Heino Laidmaa v Mart Martin | W | 3-2 |
| TT Cup (2023) | 2023/08/24 10:15 | Koit Karjus v Heino Laidmaa | W | 0-3 |
| TT Cup (2023) | 2023/08/23 13:15 | Heino Laidmaa v Koit Karjus | L | 2-3 |
| 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 |
| TT Cup (2023) | 2023/08/25 18:45 | Toivo Tuisk v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/08/25 17:45 | Toivo Tuisk v Oliver Ollman | L | 3-1 |
| TT Cup (2023) | 2023/08/25 16:45 | Oliver Ollman v Raul Pirson | W | 3-1 |
| TT Cup (2023) | 2023/08/25 15:15 | Aleksandr Sokirjanski v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/08/22 18:45 | Mart Martin v Oliver Ollman | L | 3-0 |