| TT Cup | 08/17 10:45 | - | Urmas Roos v Edvinas Tamashauskas | L | 0-3 | |
| TT Cup | 08/12 08:45 | - | Urmas Roos v Mart Ojamaa | W | 3-1 | |
| TT Cup | 08/12 07:45 | - | Valdek Putkemaa v Urmas Roos | L | 3-2 | |
| TT Cup | 08/12 06:45 | - | Mart Ojamaa v Urmas Roos | W | 1-3 | |
| TT Cup | 08/12 05:45 | - | Vootele Vaher v Urmas Roos | L | 3-1 | |
| TT Cup | 08/08 09:15 | - | Martin Pakk v Urmas Roos | L | 3-1 | |
| TT Cup | 08/08 08:15 | - | Mart Ojamaa v Urmas Roos | W | 0-3 | |
| TT Cup | 08/08 07:45 | - | Urmas Roos v Martin Pakk | L | 1-3 | |
| TT Cup | 08/08 06:15 | - | Urmas Roos v Tonu Kanne | W | 3-1 | |
| TT Cup | 08/04 08:45 | - | Vootele Vaher v Urmas Roos | L | 3-2 | |
| TT Cup | 08/04 08:15 | - | Urmas Roos v Valdek Putkemaa | L | 2-3 | |
| TT Cup | 08/04 07:15 | - | Urmas Roos v Vootele Vaher | L | 1-3 | |
| TT Cup | 08/04 06:45 | - | Urmas Roos v Johannes Kant | L | 2-3 | |
| TT Cup | 08/03 08:45 | - | Johannes Kant v Urmas Roos | L | 3-1 | |
| TT Cup | 08/03 07:15 | - | Heldur Nermann v Urmas Roos | W | 1-3 | |
| TT Cup | 08/03 06:15 | - | Johannes Kant v Urmas Roos | L | 3-0 | |
| TT Cup | 08/03 05:45 | - | Urmas Roos v Martin Pakk | L | 2-3 | |
| TT Cup | 07/25 08:45 | - | Johannes Kant v Urmas Roos | L | 3-1 | |
| TT Cup | 07/25 07:15 | - | Johannes Kant v Urmas Roos | L | 3-0 | |
| TT Cup | 07/25 06:15 | - | Martin Pakk v Urmas Roos | L | 3-1 | |
| TT Cup | 07/25 05:45 | - | Urmas Roos v Mart Ojamaa | L | 0-3 | |
| TT Cup | 07/21 13:15 | - | Urmas Roos v Jevgeni Sikorski | W | 3-2 | |
| TT Cup | 07/21 12:15 | - | Jevgeni Sikorski v Urmas Roos | W | 0-3 | |
| TT Cup | 07/21 11:15 | - | Meelis Kreegi v Urmas Roos | L | 3-1 | |
| TT Cup | 07/21 10:15 | - | Timo Siim v Urmas Roos | L | 3-0 | |
| TT Cup | 07/20 08:45 | - | Urmas Roos v Vootele Vaher | W | 3-2 | |
| TT Cup | 07/20 07:45 | - | Kalle Kask v Urmas Roos | L | 3-1 | |
| TT Cup | 07/20 06:45 | - | Johannes Kant v Urmas Roos | L | 3-1 | |
| TT Cup | 07/20 05:45 | - | Vootele Vaher v Urmas Roos | W | 1-3 | |
| TT Cup | 06/27 13:45 | - | Vootele Vaher v Urmas Roos | L | 3-1 |