| TT Cup | 12/11 17:45 | - | Oliver Ollmann v Nikolai Danilov | W | 3-0 | |
| TT Cup | 12/11 16:15 | - | Valdek Putkemaa v Oliver Ollman | W | 1-3 | |
| TT Cup | 12/07 09:55 | - | Vootele Vaher v Oliver Ollmann | L | 3-2 | |
| TT Cup | 12/07 08:45 | - | Oliver Ollmann v Yuto Kobayashi | L | 1-3 | |
| TT Cup | 12/07 07:45 | - | Oliver Ollmann v Vootele Vaher | L | 1-3 | |
| TT Cup | 12/07 06:45 | - | Oliver Ollmann v Edvinas Tamashauskas | W | 3-1 | |
| TT Cup | 12/05 10:25 | - | Oliver Ollman v Yuto Kobayashi | L | 2-3 | |
| TT Cup | 12/05 08:45 | - | Vincent Oberle v Oliver Ollman | W | 1-3 | |
| TT Cup | 12/05 08:15 | - | Edvinas Tamashauskas v Oliver Ollman | W | 0-3 | |
| TT Cup | 12/05 07:15 | - | Oliver Ollman v Yuto Kobayashi | W | 3-1 | |
| TT Cup | 11/29 14:20 | - | Meelis Apsolon v Oliver Ollman | W | 0-3 | |
| TT Cup | 11/29 13:15 | - | Oliver Ollman v Stanislav Kruti | L | 2-3 | |
| TT Cup | 11/29 12:15 | - | Oliver Ollman v Meelis Apsolon | L | 2-3 | |
| TT Cup | 11/29 11:15 | - | Oliver Ollman v Andrus Steinbach | L | 0-3 | |
| TT Cup | 11/27 10:20 | - | Mart Martin v Oliver Ollman | - | Cancelled | |
| TT Cup | 11/27 09:50 | - | Vincent Oberle v Oliver Ollman | W | 2-3 | |
| TT Cup | 11/27 09:15 | - | Oliver Ollman v Vootele Vaher | L | 1-3 | |
| TT Cup | 11/27 07:45 | - | Mart Martin v Oliver Ollman | W | 1-3 | |
| TT Cup | 11/27 07:15 | - | Vincent Oberle v Oliver Ollman | L | 3-0 | |
| TT Cup | 11/21 19:50 | - | Oliver Ollman v Raul Pirson | W | 3-2 | |
| TT Cup | 11/21 18:15 | - | Oliver Ollman v Raul Pirson | W | 3-1 | |
| TT Cup | 11/21 17:15 | - | Oliver Ollman v Aleksei Nedostojev | W | 3-1 | |
| TT Cup | 11/21 16:15 | - | Oliver Ollman v Aleksandr Sokirjanski | W | 3-0 | |
| TT Cup | 11/20 20:05 | - | Oliver Ollman v Toivo Tuisk | W | 3-1 | |
| TT Cup | 11/20 18:15 | - | Oliver Ollman v Raul Pirson | W | 3-1 | |
| TT Cup | 11/20 17:15 | - | Oliver Ollman v Toivo Tuisk | W | 3-0 | |
| TT Cup | 11/20 16:15 | - | Oliver Ollman v Valdek Putkemaa | W | 3-0 | |
| TT Cup | 11/13 19:50 | - | Oliver Ollman v Raul Pirson | W | 3-0 | |
| TT Cup | 11/13 18:45 | - | Raul Pirson v Oliver Ollman | W | 0-3 | |
| TT Cup | 11/13 17:45 | - | Oliver Ollman v Heino Laidmaa | W | 3-1 |