Round: 26 Ground: Clay
| ITF Estonia F2 | 2016/10/25 15:00 | Vitaly Kozyukov v Kenneth Raisma | 3-6,6-3,3-6 |
| ITF Sweden F5 | 2016/10/05 12:00 | Kenneth Raisma v Tim Van Rijthoven | 2-6,6-3,2-6 |
| ITF Sweden F5 | 2016/10/04 15:10 | Kenneth Raisma v Fred Simonsson | 6-3,7-5 |
| ITF Sweden F4 | 2016/09/28 08:00 | Markus Eriksson v Kenneth Raisma | 6-4,6-0 |
| ITF Sweden F4 | 2016/09/27 10:35 | Kenneth Raisma v Christian Samuelsson | 6-3,7-6 |
| ITF Estonia F1 | 2016/07/26 22:00 | Kenneth Raisma v Mikelis Libietis | 6-7,3-6 |
| ITF Estonia F1 | 2016/07/25 22:00 | Kenneth Raisma v Tadas Babelis | 6-4,5-7,6-3 |
| ITF Italy F14 | 2016/06/08 11:35 | Christopher O'Connell v Kenneth Raisma | 2-6,7-6,6-3 |
| ITF Estonia F2 | 2016/10/24 13:00 | Verneri Tuomi v Mattias Siimar | 3-6,0-6 |
| ITF Estonia F1 | 2016/07/26 22:00 | Yann Wojcik v Mattias Siimar | 7-5,7-6 |
| ITF Estonia F1 | 2016/07/25 22:00 | Mattias Siimar v Karl Kiur Saar | 2-6,6-3,6-3 |
| ITF Estonia F1 | 2015/11/11 13:25 | Vladimir Ivanov v Mattias Siimar | 6-4,6-7,6-2 |
| ITF Estonia F1 | 2015/11/09 08:00 | Krisjanis Stabins v Mattias Siimar | 6-1,6-7,4-6 |
| ITF Estonia F3 | 2015/11/03 13:00 | Niels Lootsma v Mattias Siimar | 6-4,6-3 |
| ITF Estonia F2 | 2015/10/30 15:15 | Mattias Siimar v Filip Horanský | 2-6,3-6 |
| ITF Estonia F2 | 2015/10/29 12:00 | Alexander Vasilenko v Mattias Siimar | 3-6,5-7 |