| TT Cup | 2023/01/17 08:15 | Oliver Ollman v Oleg Gussarov | W | 3-0 |
| TT Cup | 2023/01/09 07:15 | Oleg Gussarov v Oliver Ollman | W | 0-3 |
| TT Cup | 2022/07/03 05:45 | Oliver Ollman v Oleg Gussarov | L | 0-3 |
| TT Cup | 2023/06/12 16:15 | Enno Vinne v Oliver Ollman | W | 0-3 |
| TT Cup | 2023/06/12 15:45 | Raul Pirson v Oliver Ollman | W | 1-3 |
| TT Cup | 2023/06/01 18:45 | Vootele Vaher v Oliver Ollman | W | 2-3 |
| TT Cup | 2023/06/01 17:15 | Vootele Vaher v Oliver Ollman | L | 3-0 |
| TT Cup | 2023/06/01 16:45 | Toivo Tuisk v Oliver Ollman | W | 1-3 |
| TT Cup | 2023/06/01 15:45 | Oliver Ollman v Raul Pirson | W | 3-1 |
| TT Cup | 2023/05/12 13:45 | Dmitri Donskov v Oliver Ollman | L | 3-0 |
| TT Cup | 2023/05/12 12:15 | Oliver Ollman v Valdek Putkemaa | W | 3-1 |
| TT Cup | 2023/06/12 16:45 | Oleg Gussarov v Raul Pirson | L | 0-3 |
| TT Cup | 2023/06/12 15:15 | Enno Vinne v Oleg Gussarov | L | 3-1 |
| TT Cup | 2023/06/01 07:11 | Heino Laidmaa v Oleg Gussarov | L | 3-2 |
| TT Cup | 2023/06/01 06:55 | Heino Laidmaa v Oleg Gussarov | L | 3-2 |
| TT Cup | 2023/06/01 05:45 | Vadim Strogov v Oleg Gussarov | L | 3-2 |
| TT Cup | 2023/05/03 08:45 | Mart Ojamaa v Oleg Gussarov | L | 3-2 |
| TT Cup | 2023/05/03 07:45 | Raul Pirson v Oleg Gussarov | L | 3-0 |
| TT Cup | 2023/05/03 07:15 | Martin Pakk v Oleg Gussarov | L | 3-0 |