| TT Cup | 06/27 12:45 | - | Oleg Gussarov v Urmas Roos | W | 0-3 | |
| TT Cup | 06/27 12:15 | - | Urmas Roos v Margus Joelaid | W | 3-1 | |
| TT Cup | 06/27 10:45 | - | Urmas Roos v Vootele Vaher | L | 1-3 | |
| TT Cup | 06/23 13:15 | - | Urmas Roos v Oleg Gussarov | W | 3-1 | |
| TT Cup | 06/23 12:45 | - | Oleg Gussarov v Urmas Roos | W | 0-3 | |
| TT Cup | 06/23 12:15 | - | Urmas Roos v Johannes Kant | L | 1-3 | |
| TT Cup | 06/23 10:45 | - | Urmas Roos v Mart Ojamaa | L | 1-3 | |
| TT Cup | 06/18 09:15 | - | Johannes Kant v Urmas Roos | L | 3-1 | |
| TT Cup | 06/18 08:15 | - | Heldur Nermann v Urmas Roos | W | 0-3 | |
| TT Cup | 06/18 07:45 | - | Urmas Roos v Johannes Kant | L | 1-3 | |
| TT Cup | 06/18 06:15 | - | Urmas Roos v Oliver Ollman | W | 3-2 | |
| TT Cup | 06/14 08:45 | - | Urmas Roos v Aleksei Runov | W | 3-0 | |
| TT Cup | 06/14 08:15 | - | Vladyslav Rybachok v Urmas Roos | L | 3-0 | |
| TT Cup | 06/14 07:45 | - | Urmas Roos v Aleksei Runov | W | 3-2 | |
| TT Cup | 06/14 06:15 | - | Urmas Roos v Vincent Oberle | L | 0-3 | |
| TT Cup | 06/13 13:15 | - | Urmas Roos v Vootele Vaher | W | 3-1 | |
| TT Cup | 06/13 12:45 | - | Vootele Vaher v Urmas Roos | W | 0-3 | |
| TT Cup | 06/13 12:15 | - | Urmas Roos v Johannes Kant | L | 0-3 | |
| TT Cup | 06/13 10:45 | - | Urmas Roos v Aleksei Runov | L | 1-3 | |
| TT Cup | 05/31 13:15 | - | Urmas Roos v Lauri Ulla | L | 1-3 | |
| TT Cup | 05/31 11:45 | - | Lauri Ulla v Urmas Roos | W | 0-3 | |
| TT Cup | 05/31 10:45 | - | Anton Kukeste v Urmas Roos | L | 3-1 | |
| TT Cup | 05/31 10:15 | - | Urmas Roos v Martin Pakk | L | 0-3 | |
| TT Cup | 05/30 13:45 | - | Urmas Roos v Oleg Gussarov | L | 2-3 | |
| TT Cup | 05/30 12:15 | - | Oleg Gussarov v Urmas Roos | W | 2-3 | |
| TT Cup | 05/30 11:15 | - | Lembit Laumets v Urmas Roos | L | 3-2 | |
| TT Cup | 05/30 10:15 | - | Margus Joelaid v Urmas Roos | W | 1-3 | |
| TT Cup | 05/26 09:15 | - | Urmas Roos v Aleksandr Sokirjanski | L | 2-3 | |
| TT Cup | 05/26 07:45 | - | Oliver Ollman v Urmas Roos | L | 3-1 | |
| TT Cup | 05/26 06:45 | - | Martin Printsmann v Urmas Roos | W | 0-3 |