Round: 27 Ground: Hardcourt indoor
| ITF Estonia F4 | 2016/11/08 23:00 | Viktor Durasovic v Shane Vinsant | 5-7,2-6 |
| ITF Estonia F4 | 2016/11/05 23:00 | Shane Vinsant v Tadas Babelis | 4-6,7-6,6-4 |
| ITF Estonia F4 | 2016/11/04 23:00 | Shane Vinsant v Verneri Tuomi | 7-6,6-3 |
| ITF Estonia F3 | 2016/11/02 15:20 | Dzmitry Zhyrmont v Shane Vinsant | 6-4,6-2 |
| ITF Estonia F3 | 2016/10/31 11:30 | Robertas Vrzesinski v Shane Vinsant | 2-6,1-6 |
| ITF Estonia F3 | 2016/10/30 09:00 | Shane Vinsant v Timur Kiyamov | 5-7,7-5,6-1 |
| ITF Estonia F3 | 2016/10/29 13:00 | Shane Vinsant v Ville-Petteri Ahti | 6-1,4-6,6-2 |
| ITF Estonia F2 | 2016/10/25 11:00 | Shane Vinsant v Andrea Basso | 3-6,7-6,3-6 |
| ITF Estonia F4 | 2016/11/09 09:54 | Niels Lootsma v Markus Eriksson | 7-6,6-3 |
| ITF Estonia F4 | 2016/11/08 23:00 | Niels Lootsma v Markus Eriksson | 7-6,6-3 |
| ITF Estonia F3 | 2016/11/06 09:00 | Niels Lootsma v Marat Deviatiarov | 6-2,6-4 |
| ITF Estonia F3 | 2016/11/05 12:25 | Alexander Vasilenko v Niels Lootsma | 3-6,6-3,3-6 |
| ITF Estonia F3 | 2016/11/04 13:25 | Niels Lootsma v Vladimir Ivanov | 7-5,6-3 |
| ITF Estonia F3 | 2016/11/02 11:00 | Temur Ismailov v Niels Lootsma | 3-6,6-2,0-6 |
| ITF Estonia F3 | 2016/10/31 12:05 | Bart Stevens v Niels Lootsma | 3-6,4-6 |
| ITF Czech Republic F8 | 2016/10/23 08:00 | Niels Lootsma v Petr Michnev | 6-7,5-7 |