| TT Cup (2023) | 2023/10/27 15:15 | Oliver Ollman v Valdek Putkemaa | W | 3-1 |
| TT Cup (2023) | 2023/10/09 18:45 | Oliver Ollman v Valdek Putkemaa | W | 3-1 |
| TT Cup (2023) | 2023/10/09 15:15 | Valdek Putkemaa v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/10/06 18:50 | Oliver Ollman v Valdek Putkemaa | L | 1-3 |
| TT Cup (2023) | 2023/10/06 17:45 | Valdek Putkemaa v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/09/29 18:45 | Oliver Ollman v Valdek Putkemaa | L | 1-3 |
| TT Cup (2023) | 2023/09/29 15:15 | Oliver Ollman v Valdek Putkemaa | W | 3-0 |
| TT Cup (2023) | 2023/05/12 12:15 | Oliver Ollman v Valdek Putkemaa | W | 3-1 |
| TT Cup (2023) | 2023/11/13 19:50 | Oliver Ollman v Raul Pirson | W | 3-0 |
| TT Cup (2023) | 2023/11/13 18:45 | Raul Pirson v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/11/13 17:45 | Oliver Ollman v Heino Laidmaa | W | 3-1 |
| TT Cup (2023) | 2023/11/13 16:15 | Toivo Tuisk v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/10/30 19:50 | Oliver Ollman v Madis Vaarpu | W | 3-0 |
| TT Cup (2023) | 2023/10/30 18:15 | Madis Vaarpu v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/10/30 17:45 | Konstantin Akimov v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/10/30 16:45 | Oliver Ollman v Eduard Pukkonen | W | 3-2 |
| TT Cup (2023) | 2023/11/16 19:25 | Valdek Putkemaa v Brunold Oja | W | 3-1 |
| TT Cup (2023) | 2023/11/16 18:15 | Valdek Putkemaa v Heino Laidmaa | L | 1-3 |
| TT Cup (2023) | 2023/11/16 17:15 | Valdek Putkemaa v Brunold Oja | W | 3-1 |
| TT Cup (2023) | 2023/11/16 16:15 | Valdek Putkemaa v Dmitry Fomichenko | L | 0-3 |
| TT Cup (2023) | 2023/11/07 19:50 | Valdek Putkemaa v Brunold Oja | W | 3-0 |
| TT Cup (2023) | 2023/11/07 18:15 | Oleg Gussarov v Valdek Putkemaa | W | 1-3 |
| TT Cup (2023) | 2023/11/07 17:45 | Aleksandr Sokirjanski v Valdek Putkemaa | W | 1-3 |
| TT Cup (2023) | 2023/11/07 16:45 | Valdek Putkemaa v Brunold Oja | W | 3-1 |