| TT Cup (2023) | 05/16 18:15 | - | Valerii Ignatev v Timo Siim | W | 2-3 | |
| TT Cup (2023) | 05/16 17:15 | - | Valerii Ignatev v Timo Siim | L | 3-1 | |
| TT Cup (2023) | 05/16 16:45 | - | Peetr Viigimets v Timo Siim | L | 3-1 | |
| TT Cup (2023) | 05/16 15:45 | - | Timo Siim v Edvinas Tamashauskas | L | 1-3 | |
| TT Cup (2023) | 01/27 19:15 | - | Timo Siim v Arvi Tammoja | L | 1-3 | |
| TT Cup (2023) | 01/27 18:15 | - | Edvinas Tamashauskas v Timo Siim | L | 3-0 | |
| TT Cup (2023) | 01/27 17:45 | - | Arvi Tammoja v Timo Siim | W | 2-3 | |
| TT Cup (2023) | 01/27 16:45 | - | Timo Siim v Vladimir Sastin | W | 3-2 | |
| TT Cup (2023) | 01/21 14:45 | - | Timo Siim v Oliver Ollman | W | 3-0 | |
| TT Cup (2023) | 01/21 13:45 | - | Timo Siim v Meelis Kreegi | L | 1-3 | |
| TT Cup (2023) | 01/21 11:45 | - | Timo Siim v Oliver Ollman | W | 3-1 | |
| TT Cup (2023) | 01/21 11:15 | - | Timo Siim v Raul Pirson | W | 3-1 |