| 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) | 2023/10/13 15:15 | Dmitry Fomichenko v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/10/09 18:45 | Oliver Ollman v Valdek Putkemaa | W | 3-1 |
| TT Cup (2023) | 2023/10/09 17:45 | Konstantin Akimov v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/10/09 16:45 | Oliver Ollman v Brunold Oja | W | 3-0 |
| TT Cup (2023) | 2023/10/09 15:15 | Valdek Putkemaa v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/10/16 18:50 | Madis Vaarpu v Valdek Putkemaa | L | 1-3 |
| TT Cup (2023) | 2023/10/16 17:45 | Madis Vaarpu v Konstantin Akimov | W | 3-2 |
| TT Cup (2023) | 2023/10/16 16:15 | Valdek Putkemaa v Madis Vaarpu | W | 2-3 |
| TT Cup (2023) | 2023/10/16 15:45 | Brunold Oja v Madis Vaarpu | W | 0-3 |
| TT Cup (2023) | 2023/10/11 13:15 | Martin Pakk v Madis Vaarpu | L | 3-1 |
| TT Cup (2023) | 2023/10/11 12:45 | Madis Vaarpu v Oleg Gussarov | L | 0-3 |
| TT Cup (2023) | 2023/10/11 11:15 | Martin Pakk v Madis Vaarpu | W | 2-3 |
| TT Cup (2023) | 2023/10/11 10:45 | Mart Ojamaa v Madis Vaarpu | L | 3-0 |