| TT Cup (2023) | 2023/05/12 12:15 | Oliver Ollman v Valdek Putkemaa | W | 3-1 |
| TT Cup (2023) | 2023/03/13 09:45 | Valdek Putkemaa v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/03/13 07:45 | Oliver Ollman v Valdek Putkemaa | L | 2-3 |
| TT Cup (2023) | 2023/02/28 07:15 | Valdek Putkemaa v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/02/20 09:45 | Oliver Ollman v Valdek Putkemaa | L | 1-3 |
| TT Cup (2023) | 2023/02/20 08:15 | Oliver Ollman v Valdek Putkemaa | W | 3-2 |
| TT Cup (2023) | 2023/02/13 08:15 | Oliver Ollman v Valdek Putkemaa | L | 0-3 |
| 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) | 2023/08/28 16:45 | Oliver Ollman v Vootele Vaher | L | 0-3 |
| TT Cup (2023) | 2023/08/28 15:15 | Raul Pirson v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/08/25 18:45 | Toivo Tuisk v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/08/25 17:45 | Toivo Tuisk v Oliver Ollman | L | 3-1 |
| TT Cup (2023) | 2023/08/25 16:45 | Oliver Ollman v Raul Pirson | W | 3-1 |
| TT Cup (2023) | 2023/08/25 15:15 | Aleksandr Sokirjanski v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/09/20 13:45 | Valdek Putkemaa v Mart Ojamaa | W | 3-2 |
| TT Cup (2023) | 2023/09/20 12:45 | Valdek Putkemaa v Kestutis Aleknavicius | W | 3-1 |
| TT Cup (2023) | 2023/09/20 11:15 | Mart Ojamaa v Valdek Putkemaa | W | 1-3 |
| TT Cup (2023) | 2023/09/20 10:45 | Heldur Nermann v Valdek Putkemaa | W | 1-3 |
| TT Cup (2023) | 2023/08/11 13:15 | Valdek Putkemaa v Mart Ojamaa | W | 3-1 |
| TT Cup (2023) | 2023/08/11 12:15 | Mart Ojamaa v Valdek Putkemaa | W | 2-3 |
| TT Cup (2023) | 2023/08/11 11:45 | Raul Pirson v Valdek Putkemaa | L | 3-0 |
| TT Cup (2023) | 2023/08/11 10:45 | Valdek Putkemaa v Johannes Kant | L | 2-3 |