| TT Cup | 2023/06/28 16:15 | Oliver Ollman v Enno Vinne | W | 3-1 |
| TT Cup | 2023/06/12 18:45 | Oliver Ollman v Enno Vinne | W | 3-1 |
| TT Cup | 2023/06/12 16:15 | Enno Vinne v Oliver Ollman | W | 0-3 |
| TT Cup | 2023/08/22 15:15 | Mart Martin v Oliver Ollman | L | 3-2 |
| TT Cup | 2023/08/16 18:15 | Raul Pirson v Oliver Ollman | W | 0-3 |
| TT Cup | 2023/08/16 17:45 | Mart Martin v Oliver Ollman | L | 3-2 |
| TT Cup | 2023/08/16 16:45 | Oliver Ollman v Heino Laidmaa | W | 3-1 |
| TT Cup | 2023/08/16 15:15 | Raul Pirson v Oliver Ollman | L | 3-0 |
| TT Cup | 2023/08/07 18:45 | Mart Martin v Oliver Ollman | W | 1-3 |
| TT Cup | 2023/08/07 17:15 | Oliver Ollman v Mart Martin | L | 2-3 |
| TT Cup | 2023/08/07 16:15 | Oliver Ollman v Raul Pirson | W | 3-0 |
| TT Cup | 2023/08/22 15:45 | Enno Vinne v Raul Pirson | W | 3-2 |
| TT Cup | 2023/07/04 18:15 | Heino Laidmaa v Enno Vinne | L | 3-1 |
| TT Cup | 2023/07/04 17:45 | Enno Vinne v Raul Pirson | L | 1-3 |
| TT Cup | 2023/07/04 16:15 | Vadim Strogov v Enno Vinne | W | 1-3 |
| TT Cup | 2023/07/04 15:45 | Heino Laidmaa v Enno Vinne | L | 3-2 |
| TT Cup | 2023/06/28 18:15 | Yuto Kobayashi v Enno Vinne | L | 3-1 |
| TT Cup | 2023/06/28 17:45 | Enno Vinne v Yuto Kobayashi | L | 0-3 |
| TT Cup | 2023/06/28 16:15 | Oliver Ollman v Enno Vinne | L | 3-1 |