| 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) | 2023/03/13 09:45 | Valdek Putkemaa v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/10/19 18:55 | Oliver Ollman v Aleksandr Sokirjanski | L | 2-3 |
| TT Cup (2023) | 2023/10/19 17:15 | Aleksandr Sokirjanski v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/10/19 16:45 | Dmitry Fomichenko v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/10/19 15:45 | Oliver Ollman v Toivo Tuisk | W | 3-2 |
| TT Cup (2023) | 2023/10/13 18:50 | Dmitry Fomichenko v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/10/13 17:45 | Toivo Tuisk v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/10/13 16:45 | Oliver Ollman v Heino Laidmaa | W | 3-2 |
| TT Cup (2023) | 2023/10/13 15:15 | Dmitry Fomichenko v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/10/20 13:50 | Raul Pirson v Valdek Putkemaa | L | 3-1 |
| TT Cup (2023) | 2023/10/20 12:15 | Mart Ojamaa v Valdek Putkemaa | W | 2-3 |
| TT Cup (2023) | 2023/10/20 11:45 | Madis Vaarpu v Valdek Putkemaa | W | 1-3 |
| TT Cup (2023) | 2023/10/20 10:45 | Valdek Putkemaa v Raul Pirson | L | 1-3 |
| TT Cup (2023) | 2023/10/16 18:50 | Madis Vaarpu v Valdek Putkemaa | W | 1-3 |
| TT Cup (2023) | 2023/10/16 17:15 | Valdek Putkemaa v Brunold Oja | W | 3-1 |
| TT Cup (2023) | 2023/10/16 16:15 | Valdek Putkemaa v Madis Vaarpu | L | 2-3 |
| TT Cup (2023) | 2023/10/16 15:15 | Valdek Putkemaa v Konstantin Akimov | W | 3-2 |