| TT Cup (2023) | 2023/02/28 10:15 | Oliver Ollman v Mart Ojamaa | W | 3-0 |
| TT Cup (2023) | 2023/02/28 07:45 | Mart Ojamaa v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/02/13 09:45 | Oliver Ollman v Mart Ojamaa | W | 3-1 |
| TT Cup (2023) | 2023/02/13 09:15 | Mart Ojamaa v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/01/31 07:15 | Mart Ojamaa v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/01/10 12:15 | Mart Ojamaa v Oliver Ollman | W | 1-3 |
| TT Cup (2022) | 2022/12/20 10:15 | Mart Ojamaa v Oliver Ollman | W | 2-3 |
| TT Cup (2022) | 2022/12/20 09:15 | Mart Ojamaa v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/03/23 06:45 | Vincent Oberle v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/03/15 10:15 | Raul Pirson v Oliver Ollman | L | 3-1 |
| TT Cup (2023) | 2023/03/15 09:15 | Oliver Ollman v Raul Pirson | L | 0-3 |
| TT Cup (2023) | 2023/03/15 07:45 | Heldur Nermann v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/03/15 07:15 | Ermo Veelain v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/03/13 09:45 | Valdek Putkemaa v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/03/13 08:45 | Oliver Ollman v Raul Pirson | W | 3-0 |
| TT Cup (2023) | 2023/03/13 07:45 | Oliver Ollman v Valdek Putkemaa | L | 2-3 |
| TT Cup (2023) | 2023/03/23 07:15 | Mart Ojamaa v Raul Pirson | L | 0-3 |
| TT Cup (2023) | 2023/03/21 10:15 | Vincent Oberle v Mart Ojamaa | L | 3-2 |
| TT Cup (2023) | 2023/03/21 09:15 | Ermo Veelain v Mart Ojamaa | W | 2-3 |
| TT Cup (2023) | 2023/03/21 08:15 | Mart Ojamaa v Madis Vaarpu | W | 3-2 |
| TT Cup (2023) | 2023/03/21 06:45 | Vincent Oberle v Mart Ojamaa | L | 3-0 |
| TT Cup (2023) | 2023/03/14 14:45 | Mart Ojamaa v Martin Pakk | W | 3-2 |
| TT Cup (2023) | 2023/03/14 13:15 | Mart Ojamaa v Eduard Pukkonen | W | 3-1 |
| TT Cup (2023) | 2023/03/14 12:15 | Mart Ojamaa v Madis Vaarpu | W | 3-2 |