| 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 |