Round: 29 Ground: Clay
| ITF Estonia F1 | 2015/08/01 11:20 | Kenneth Raisma v Vladimir Ivanov | 6-7,6-7 |
| 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 |
| Challenger Tashkent Qual | 2016/10/09 07:25 | Alexander Vasilenko v Vladimir Ivanov | 7-6,6-4 |
| Challenger Tashkent Qual | 2016/10/08 09:05 | Pavel Petrov v Vladimir Ivanov | 5-7,2-6 |
| ITF Kazakhstan F7 | 2016/10/06 05:50 | Vladimir Ivanov v Alexander Igoshin | 6-4,6-7,0-6 |
| ITF Kazakhstan F7 | 2016/10/05 05:15 | Vladimir Ivanov v Grigoriy Lomakin | 4-6,6-0,6-1 |
| ITF Estonia F2 | 2016/10/29 11:30 | Alexander Igoshin v Kenneth Raisma | 3-6,6-7 |
| ITF Estonia F2 | 2016/10/28 14:00 | Kenneth Raisma v Krisjanis Stabins | 7-5,7-5 |
| ITF Estonia F2 | 2016/10/27 14:30 | Kenneth Raisma v Mattias Siimar | 6-1,6-4 |
| 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 |