| 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 | |
| TT Cup (2022) | 12/27 13:15 | - | Johannes Kant v Timo Siim | - | Cancelled | |
| TT Cup (2022) | 12/27 12:45 | - | Gerrit Hallmagi v Timo Siim | - | Cancelled | |
| TT Cup (2022) | 12/27 11:45 | - | Timo Siim v Martin Salong | D | Cancelled | |
| TT Cup (2022) | 11/25 14:45 | - | Timo Siim v Edvinas Tamashauskas | L | 2-3 | |
| TT Cup (2022) | 11/25 13:15 | - | Martin Salong v Timo Siim | W | 0-3 | |
| TT Cup (2022) | 11/25 12:45 | - | Edvinas Tamashauskas v Timo Siim | W | 0-3 | |
| TT Cup (2022) | 11/25 11:45 | - | Timo Siim v Oleg Jefremov | W | 3-2 | |
| TT Cup (2022) | 11/16 10:15 | - | Timo Siim v Vootele Vaher | W | 3-1 | |
| TT Cup (2022) | 11/16 09:15 | - | Vootele Vaher v Timo Siim | W | 0-3 | |
| TT Cup (2022) | 11/16 08:15 | - | Timo Siim v Johannes Kant | W | 3-0 | |
| TT Cup (2022) | 11/16 06:45 | - | Martin Pakk v Timo Siim | L | 3-0 | |
| TT Cup (2022) | 10/13 09:15 | - | Timo Siim v Heiki Sullakatko | W | 3-2 | |
| TT Cup (2022) | 10/13 08:15 | - | Timo Siim v Heiki Sullakatko | W | 3-2 | |
| TT Cup (2022) | 10/13 06:45 | - | Vootele Vaher v Timo Siim | W | 1-3 | |
| TT Cup (2022) | 10/13 06:15 | - | Rene Kaljuvee v Timo Siim | W | 0-3 | |
| TT Cup (2022) | 09/17 09:15 | - | Timo Siim v Mart Vaarpu | L | 0-3 | |
| TT Cup (2022) | 09/17 08:15 | - | Meelis Apsolon v Timo Siim | W | 2-3 | |
| TT Cup (2022) | 09/17 07:15 | - | Timo Siim v Mart Vaarpu | W | 3-2 |