| TT Cup (2023) | 2023/03/13 09:45 | Valdek Putkemaa v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/03/13 07:45 | Oliver Ollman v Valdek Putkemaa | L | 2-3 |
| TT Cup (2023) | 2023/02/28 07:15 | Valdek Putkemaa v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/02/20 09:45 | Oliver Ollman v Valdek Putkemaa | L | 1-3 |
| TT Cup (2023) | 2023/02/20 08:15 | Oliver Ollman v Valdek Putkemaa | W | 3-2 |
| TT Cup (2023) | 2023/02/13 08:15 | Oliver Ollman v Valdek Putkemaa | L | 0-3 |
| TT Cup (2023) | 2023/05/12 11:15 | Oliver Ollman v Dmitri Donskov | L | 0-3 |
| TT Cup (2023) | 2023/05/12 10:15 | Oliver Ollman v Yuto Kobayashi | W | 3-1 |
| TT Cup (2023) | 2023/03/29 09:15 | Stanislav Kruti v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/03/29 07:45 | Vincent Oberle v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/03/29 07:15 | Martin Pakk v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/03/29 06:15 | Oliver Ollman v Stanislav Kruti | L | 2-3 |
| TT Cup (2023) | 2023/03/23 10:15 | Oliver Ollman v Vincent Oberle | L | 0-3 |
| TT Cup (2023) | 2023/03/23 09:15 | Raul Pirson v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/05/12 11:45 | Yuto Kobayashi v Valdek Putkemaa | L | 3-2 |
| TT Cup (2023) | 2023/05/12 10:45 | Valdek Putkemaa v Dmitri Donskov | L | 0-3 |
| TT Cup (2023) | 2023/05/08 09:15 | Vincent Oberle v Valdek Putkemaa | W | 2-3 |
| TT Cup (2023) | 2023/05/08 07:45 | Vincent Oberle v Valdek Putkemaa | L | 3-2 |
| TT Cup (2023) | 2023/05/08 07:15 | Yuto Kobayashi v Valdek Putkemaa | W | 0-3 |
| TT Cup (2023) | 2023/05/08 06:15 | Valdek Putkemaa v Mart Ojamaa | W | 3-0 |
| TT Cup (2023) | 2023/05/02 13:15 | Valdek Putkemaa v Mart Ojamaa | W | 3-2 |
| TT Cup (2023) | 2023/05/02 12:15 | Johannes Kant v Valdek Putkemaa | L | 3-2 |