Round: 26 Ground: Hardcourt indoor
| ITF Estonia F4 | 2016/11/07 23:00 | Vladimir Ivanov v Milos Sekulic | 3-6,7-5,7-6 |
| ITF Estonia F3 | 2016/11/04 13:25 | Niels Lootsma v Vladimir Ivanov | 7-5,6-3 |
| ITF Estonia F3 | 2016/11/03 14:50 | Karol Beck v Vladimir Ivanov | 3-6,5-7 |
| ITF Estonia F3 | 2016/11/01 13:25 | Kristofer Siimar v Vladimir Ivanov | 0-6,4-6 |
| ITF Estonia F2 | 2016/10/30 10:00 | Vladimir Ivanov v Kenneth Raisma | 4-6,3-6 |
| ITF Estonia F2 | 2016/10/29 09:00 | Dzmitry Zhyrmont v Vladimir Ivanov | 3-6,7-6,2-6 |
| ITF Estonia F2 | 2016/10/28 12:30 | Vladimir Ivanov v Andrea Basso | 6-2,6-4 |
| ITF Estonia F2 | 2016/10/27 13:00 | Vladimir Ivanov v Oskar Lusti | 6-0,6-0 |
| ITF Estonia F4 | 2016/11/07 23:00 | Matvey Khomentovskiy v Ivan Davydov | 7-6,6-1 |
| ITF Estonia F4 | 2016/11/04 23:00 | Matvey Khomentovskiy v Oskar Irdoja | 6-1,6-0 |
| ITF Germany F17 | 2016/10/31 09:00 | Matvey Khomentovskiy v Jochen Bertsch | 6-3,3-6,2-6 |
| ITF Germany F15 | 2016/10/20 12:30 | Matvey Khomentovskiy v Jurij Rodionov | 6-3,5-7,6-7 |
| ITF Germany F15 | 2016/10/18 09:00 | David Pichler v Matvey Khomentovskiy | 6-4,4-6,5-7 |
| ITF Germany F15 | 2016/10/16 11:00 | Matvey Khomentovskiy v David Mrazek | 6-1,3-6,6-1 |
| ITF Germany F14 | 2016/10/12 10:00 | Matvey Khomentovskiy v Louis Wessels | 2-6,2-6 |
| ITF Germany F14 | 2016/10/10 10:00 | Matvey Khomentovskiy v Yannick Stephan Born | 3-6,6-3,7-6 |