| TT Cup | 07/01 10:45 | - | Yuto Kobayashi v Oliver Ollman | L | 3-2 | |
| TT Cup | 06/28 18:45 | - | Toivo Tuisk v Oliver Ollman | L | 3-1 | |
| TT Cup | 06/28 17:15 | - | Oliver Ollman v Toivo Tuisk | W | 3-2 | |
| TT Cup | 06/28 16:15 | - | Oliver Ollman v Enno Vinne | W | 3-1 | |
| TT Cup | 06/28 15:15 | - | Oliver Ollman v Yuto Kobayashi | L | 2-3 | |
| TT Cup | 06/12 18:45 | - | Oliver Ollman v Enno Vinne | W | 3-1 | |
| TT Cup | 06/12 17:45 | - | Oliver Ollman v Oleg Gussarov | W | 3-0 | |
| TT Cup | 06/12 16:15 | - | Enno Vinne v Oliver Ollman | W | 0-3 | |
| TT Cup | 06/12 15:45 | - | Raul Pirson v Oliver Ollman | W | 1-3 | |
| TT Cup | 06/01 18:45 | - | Vootele Vaher v Oliver Ollman | W | 2-3 | |
| TT Cup | 06/01 17:15 | - | Vootele Vaher v Oliver Ollman | L | 3-0 | |
| TT Cup | 06/01 16:45 | - | Toivo Tuisk v Oliver Ollman | W | 1-3 | |
| TT Cup | 06/01 15:45 | - | Oliver Ollman v Raul Pirson | W | 3-1 | |
| TT Cup | 05/12 13:45 | - | Dmitri Donskov v Oliver Ollman | L | 3-0 | |
| TT Cup | 05/12 12:15 | - | Oliver Ollman v Valdek Putkemaa | W | 3-1 | |
| TT Cup | 05/12 11:15 | - | Oliver Ollman v Dmitri Donskov | L | 0-3 | |
| TT Cup | 05/12 10:15 | - | Oliver Ollman v Yuto Kobayashi | W | 3-1 | |
| TT Cup | 04/04 08:15 | - | Vincent Oberle v Oliver Ollman | - | Cancelled | |
| TT Cup | 04/04 07:15 | - | Oliver Ollman v Yuto Kobayashi | - | Cancelled | |
| TT Cup | 04/04 05:45 | - | Vootele Vaher v Oliver Ollman | D | Cancelled | |
| TT Cup | 03/29 09:15 | - | Stanislav Kruti v Oliver Ollman | L | 3-0 | |
| TT Cup | 03/29 07:45 | - | Vincent Oberle v Oliver Ollman | L | 3-2 | |
| TT Cup | 03/29 07:15 | - | Martin Pakk v Oliver Ollman | W | 1-3 | |
| TT Cup | 03/29 06:15 | - | Oliver Ollman v Stanislav Kruti | L | 2-3 | |
| TT Cup | 03/23 10:15 | - | Oliver Ollman v Vincent Oberle | L | 0-3 | |
| TT Cup | 03/23 09:15 | - | Raul Pirson v Oliver Ollman | W | 0-3 | |
| TT Cup | 03/23 08:15 | - | Oliver Ollman v Mart Ojamaa | W | 3-1 | |
| TT Cup | 03/23 06:45 | - | Vincent Oberle v Oliver Ollman | W | 1-3 | |
| TT Cup | 03/15 10:15 | - | Raul Pirson v Oliver Ollman | L | 3-1 | |
| TT Cup | 03/15 09:15 | - | Oliver Ollman v Raul Pirson | L | 0-3 |