| TT Cup | 07/16 05:45 | - | Oliver Ollman v Toivo Tuisk | L | 0-3 | |
| TT Cup | 07/09 08:45 | - | Oliver Ollman v Martin Printsmann | W | 3-1 | |
| TT Cup | 07/09 07:45 | - | Martin Printsmann v Oliver Ollman | W | 2-3 | |
| TT Cup | 07/09 06:45 | - | Heldur Nermann v Oliver Ollman | L | 3-2 | |
| TT Cup | 07/09 05:45 | - | Toivo Tuisk v Oliver Ollman | L | 3-2 | |
| TT Cup | 07/03 08:45 | - | Oliver Ollman v Martin Printsmann | W | 3-1 | |
| TT Cup | 07/03 07:15 | - | Martin Printsmann v Oliver Ollman | W | 2-3 | |
| TT Cup | 07/03 06:15 | - | Meelis Apsolon v Oliver Ollman | L | 3-1 | |
| TT Cup | 07/03 05:45 | - | Oliver Ollman v Oleg Gussarov | L | 0-3 | |
| TT Cup | 06/18 08:45 | - | Oliver Ollman v Heldur Nermann | L | 2-3 | |
| TT Cup | 06/18 07:15 | - | Heldur Nermann v Oliver Ollman | W | 1-3 | |
| TT Cup | 06/18 06:15 | - | Urmas Roos v Oliver Ollman | L | 3-2 | |
| TT Cup | 06/18 05:45 | - | Oliver Ollman v Johannes Kant | L | 2-3 | |
| TT Cup | 05/28 13:15 | - | Oliver Ollman v Lembit Laumets | W | 3-2 | |
| TT Cup | 05/28 11:45 | - | Aleksandr Sokirjanski v Oliver Ollman | L | 3-2 | |
| TT Cup | 05/28 10:45 | - | Lembit Laumets v Oliver Ollman | W | 1-3 | |
| TT Cup | 05/28 10:15 | - | Oliver Ollman v Meelis Apsolon | L | 1-3 | |
| TT Cup | 05/26 08:45 | - | Martin Printsmann v Oliver Ollman | W | 2-3 | |
| TT Cup | 05/26 08:15 | - | Martin Printsmann v Oliver Ollman | L | 3-1 | |
| TT Cup | 05/26 07:45 | - | Oliver Ollman v Urmas Roos | W | 3-1 | |
| TT Cup | 05/26 06:15 | - | Oliver Ollman v Aleksandr Sokirjanski | L | 0-3 |