| TT Cup | 02/07 06:45 | - | Oliver Ollman v Vincent Oberle | L | 1-3 | |
| TT Cup | 01/31 09:45 | - | Oliver Ollman v Ermo Veelain | W | 3-1 | |
| TT Cup | 01/31 09:15 | - | Oliver Ollman v Ermo Veelain | W | 3-1 | |
| TT Cup | 01/31 07:45 | - | Vincent Oberle v Oliver Ollman | L | 3-2 | |
| TT Cup | 01/31 07:15 | - | Mart Ojamaa v Oliver Ollman | L | 3-2 | |
| TT Cup | 01/28 14:15 | - | Aleksandr Dulov v Oliver Ollman | L | 3-1 | |
| TT Cup | 01/28 13:15 | - | Elvis Libene v Oliver Ollman | L | 3-0 | |
| TT Cup | 01/28 12:45 | - | Vootele Vaher v Oliver Ollman | L | 3-0 | |
| TT Cup | 01/28 11:45 | - | Oliver Ollman v Aleksandr Dulov | L | 0-3 | |
| TT Cup | 01/24 10:15 | - | Yuto Kobayashi v Oliver Ollman | W | 2-3 | |
| TT Cup | 01/24 08:45 | - | Oliver Ollman v Yuto Kobayashi | L | 1-3 | |
| TT Cup | 01/24 07:45 | - | Oliver Ollman v Raul Pirson | W | 3-2 | |
| TT Cup | 01/24 06:45 | - | Oliver Ollman v Vincent Oberle | W | 3-2 | |
| TT Cup | 01/21 14:45 | - | Timo Siim v Oliver Ollman | L | 3-0 | |
| TT Cup | 01/21 13:15 | - | Oliver Ollman v Raul Pirson | W | 3-2 | |
| TT Cup | 01/21 12:15 | - | Meelis Kreegi v Oliver Ollman | W | 0-3 | |
| TT Cup | 01/21 11:45 | - | Timo Siim v Oliver Ollman | L | 3-1 | |
| TT Cup | 01/17 10:15 | - | Oliver Ollman v Elvis Libene | W | 3-0 | |
| TT Cup | 01/17 09:15 | - | Elvis Libene v Oliver Ollman | W | 0-3 | |
| TT Cup | 01/17 08:15 | - | Oliver Ollman v Oleg Gussarov | W | 3-0 | |
| TT Cup | 01/17 06:45 | - | Yuto Kobayashi v Oliver Ollman | W | 2-3 | |
| TT Cup | 01/10 14:45 | - | Oleg Jefremov v Oliver Ollman | W | 0-3 | |
| TT Cup | 01/10 13:45 | - | Oliver Ollman v Oleg Jefremov | L | 0-3 | |
| TT Cup | 01/10 12:15 | - | Mart Ojamaa v Oliver Ollman | W | 1-3 | |
| TT Cup | 01/10 11:45 | - | Ermo Veelain v Oliver Ollman | W | 0-3 | |
| TT Cup | 01/09 10:15 | - | Oliver Ollman v Raul Pirson | L | 1-3 | |
| TT Cup | 01/09 09:15 | - | Oliver Ollman v Yuto Kobayashi | W | 3-2 | |
| TT Cup | 01/09 07:45 | - | Raul Pirson v Oliver Ollman | W | 1-3 | |
| TT Cup | 01/09 07:15 | - | Oleg Gussarov v Oliver Ollman | W | 0-3 | |
| TT Cup | 01/04 09:45 | - | Oliver Ollman v Raul Pirson | W | 3-1 |