| TT Cup (2023) | 2023/06/01 17:15 | Vootele Vaher v Oliver Ollman | W | 3-0 |
| TT Cup (2023) | 2023/03/07 19:15 | Vootele Vaher v Oliver Ollman | W | 3-0 |
| TT Cup (2023) | 2023/03/07 18:45 | Vootele Vaher v Oliver Ollman | W | 3-2 |
| TT Cup (2023) | 2023/02/09 19:15 | Vootele Vaher v Oliver Ollman | L | 2-3 |
| TT Cup (2023) | 2023/02/09 17:15 | Oliver Ollman v Vootele Vaher | W | 1-3 |
| TT Cup (2023) | 2023/01/28 12:45 | Vootele Vaher v Oliver Ollman | W | 3-0 |
| TT Cup (2023) | 2023/06/01 17:15 | Vootele Vaher v Oliver Ollman | W | 3-0 |
| TT Cup (2023) | 2023/06/01 16:15 | Vootele Vaher v Raul Pirson | W | 3-1 |
| TT Cup (2023) | 2023/06/01 15:15 | Vootele Vaher v Toivo Tuisk | W | 3-0 |
| TT Cup (2023) | 2023/05/27 13:15 | Heino Laidmaa v Vootele Vaher | W | 1-3 |
| TT Cup (2023) | 2023/05/27 12:45 | Vootele Vaher v Martin Salong | L | 2-3 |
| TT Cup (2023) | 2023/05/27 11:15 | Meelis Apsolon v Vootele Vaher | W | 1-3 |
| TT Cup (2023) | 2023/05/27 10:45 | Heino Laidmaa v Vootele Vaher | L | 3-1 |
| TT Cup (2023) | 2023/05/17 18:15 | Toivo Tuisk v Vootele Vaher | W | 1-3 |
| TT Cup (2023) | 2023/06/01 17:15 | Vootele Vaher v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/06/01 16:45 | Toivo Tuisk v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/06/01 15:45 | Oliver Ollman v Raul Pirson | W | 3-1 |
| TT Cup (2023) | 2023/05/12 13:45 | Dmitri Donskov v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/05/12 12:15 | Oliver Ollman v Valdek Putkemaa | W | 3-1 |
| TT Cup (2023) | 2023/05/12 11:15 | Oliver Ollman v Dmitri Donskov | L | 0-3 |
| TT Cup (2023) | 2023/05/12 10:15 | Oliver Ollman v Yuto Kobayashi | W | 3-1 |
| TT Cup (2023) | 2023/03/29 09:15 | Stanislav Kruti v Oliver Ollman | L | 3-0 |