| TT Cup | 11/13 16:15 | - | Toivo Tuisk v Oliver Ollman | W | 2-3 | |
| TT Cup | 10/30 19:50 | - | Oliver Ollman v Madis Vaarpu | W | 3-0 | |
| TT Cup | 10/30 18:15 | - | Madis Vaarpu v Oliver Ollman | W | 1-3 | |
| TT Cup | 10/30 17:45 | - | Konstantin Akimov v Oliver Ollman | W | 2-3 | |
| TT Cup | 10/30 16:45 | - | Oliver Ollman v Eduard Pukkonen | W | 3-2 | |
| TT Cup | 10/27 18:50 | - | Mati Krusel v Oliver Ollman | L | 3-2 | |
| TT Cup | 10/27 17:15 | - | Oliver Ollman v Mati Krusel | L | 1-3 | |
| TT Cup | 10/27 16:15 | - | Oliver Ollman v Heino Laidmaa | W | 3-1 | |
| TT Cup | 10/27 15:15 | - | Oliver Ollman v Valdek Putkemaa | W | 3-1 | |
| TT Cup | 10/19 18:55 | - | Oliver Ollman v Aleksandr Sokirjanski | L | 2-3 | |
| TT Cup | 10/19 17:15 | - | Aleksandr Sokirjanski v Oliver Ollman | W | 1-3 | |
| TT Cup | 10/19 16:45 | - | Dmitry Fomichenko v Oliver Ollman | W | 0-3 | |
| TT Cup | 10/19 15:45 | - | Oliver Ollman v Toivo Tuisk | W | 3-2 | |
| TT Cup | 10/13 18:50 | - | Dmitry Fomichenko v Oliver Ollman | L | 3-2 | |
| TT Cup | 10/13 17:45 | - | Toivo Tuisk v Oliver Ollman | W | 1-3 | |
| TT Cup | 10/13 16:45 | - | Oliver Ollman v Heino Laidmaa | W | 3-2 | |
| TT Cup | 10/13 15:15 | - | Dmitry Fomichenko v Oliver Ollman | L | 3-0 | |
| TT Cup | 10/09 18:45 | - | Oliver Ollman v Valdek Putkemaa | W | 3-1 | |
| TT Cup | 10/09 17:45 | - | Konstantin Akimov v Oliver Ollman | W | 1-3 | |
| TT Cup | 10/09 16:45 | - | Oliver Ollman v Brunold Oja | W | 3-0 | |
| TT Cup | 10/09 15:15 | - | Valdek Putkemaa v Oliver Ollman | W | 2-3 | |
| TT Cup | 10/06 18:50 | - | Oliver Ollman v Valdek Putkemaa | L | 1-3 | |
| TT Cup | 10/06 17:45 | - | Valdek Putkemaa v Oliver Ollman | W | 1-3 | |
| TT Cup | 10/06 16:45 | - | Oliver Ollman v Dmitry Fomichenko | L | 2-3 | |
| TT Cup | 10/06 15:15 | - | Heino Laidmaa v Oliver Ollman | W | 2-3 | |
| TT Cup | 09/29 18:45 | - | Oliver Ollman v Valdek Putkemaa | L | 1-3 | |
| TT Cup | 09/29 17:15 | - | Oliver Ollman v Aleksandr Sokirjanski | W | 3-1 | |
| TT Cup | 09/29 16:15 | - | Oliver Ollman v Brunold Oja | W | 3-0 | |
| TT Cup | 09/29 15:15 | - | Oliver Ollman v Valdek Putkemaa | W | 3-0 | |
| TT Cup | 08/28 18:15 | - | Heino Laidmaa v Oliver Ollman | L | 3-2 |