Round: 25 Ground: Hardcourt indoor
| 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 F2 | 2016/10/25 09:20 | Vladimir Ivanov v Shahar Elbaz | 6-1,6-0 |
| ITF Estonia F3 | 2016/10/31 09:00 | Milos Sekulic v Karol Beck | 2-6,1-6 |
| ITF Sweden F5 | 2016/10/04 12:00 | Milos Sekulic v Edward Corrie | 3-6,3-6 |
| ITF Sweden F4 | 2016/09/28 08:00 | Christopher O'Connell v Milos Sekulic | 4-6,7-6,6-0 |
| ITF Sweden F4 | 2016/09/27 09:00 | Fred Simonsson v Milos Sekulic | 6-2,1-6,1-6 |
| ITF Russia F7 | 2016/08/31 08:00 | Milos Sekulic v Yannick Mertens | 4-6,1-6 |
| ITF Russia F7 | 2016/08/30 10:15 | Milos Sekulic v Stanislav Skobelev | 7-5,6-0 |
| Challenger Prague 2 | 2016/07/24 09:00 | Matej Vocel v Milos Sekulic | 4-6,6-3,7-6 |
| Challenger Prague 2 | 2016/07/23 09:00 | Dominik Recek v Milos Sekulic | 6-7,4-6 |