| TT Cup (2023) | 2023/10/27 16:15 | Oliver Ollman v Heino Laidmaa | W | 3-1 |
| 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) | 2023/11/13 16:15 | Toivo Tuisk v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/10/30 19:50 | Oliver Ollman v Madis Vaarpu | W | 3-0 |
| TT Cup (2023) | 2023/10/30 18:15 | Madis Vaarpu v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/10/30 17:45 | Konstantin Akimov v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/10/30 16:45 | Oliver Ollman v Eduard Pukkonen | W | 3-2 |
| TT Cup (2023) | 2023/10/27 18:50 | Mati Krusel v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/10/27 17:15 | Oliver Ollman v Mati Krusel | L | 1-3 |
| TT Cup (2023) | 2023/10/27 16:15 | Oliver Ollman v Heino Laidmaa | W | 3-1 |
| TT Cup (2023) | 2023/11/13 16:45 | Heino Laidmaa v Raul Pirson | W | 3-2 |
| TT Cup (2023) | 2023/10/27 18:20 | Valdek Putkemaa v Heino Laidmaa | L | 3-2 |
| TT Cup (2023) | 2023/10/27 17:45 | Heino Laidmaa v Valdek Putkemaa | L | 1-3 |
| TT Cup (2023) | 2023/10/27 16:15 | Oliver Ollman v Heino Laidmaa | L | 3-1 |
| 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 |