Round: 62 Ground: Clay
| ITF Serbia F1 | 2016/07/20 07:30 | Christopher O'Connell v Shunsuke Wakita | 6-1,6-2 |
| ITF Macedonia F1 | 2016/07/06 12:15 | Shunsuke Wakita v Nikola Cacic | 1-6,2-6 |
| ITF Macedonia F2 | 2016/06/26 07:30 | Dejan Katic v Shunsuke Wakita | 6-1,6-1 |
| ITF Romania F5 | 2016/06/06 14:55 | Shunsuke Wakita v Philip Bachmaier | 6-2,5-7,5-7 |
| ITF Romania F5 | 2016/06/05 10:00 | Shunsuke Wakita v Vasil Yehorov | 2-6,6-2,6-3 |
| ITF Turkey F19 Qual | 2016/05/08 08:00 | Shunsuke Wakita v Vazha Shubladze | 6-2,6-2 |
| ITF Turkey F18 | 2016/05/04 11:25 | Shunsuke Wakita v Hugo Nys | 3-6,6-4,1-6 |
| ITF Turkey F18 | 2016/05/02 08:00 | Shunsuke Wakita v Cem Erturk | 7-6,6-2 |
| ITF Serbia F1 Qual | 2016/07/19 08:00 | Timo Stodder v Milos Nikolic | 6-2,6-2 |
| ITF Serbia F1 Qual | 2016/07/18 08:00 | Goran Radanovic v Milos Nikolic | 2-6,6-2,3-6 |
| ITF Macedonia F1 | 2016/07/03 08:00 | Ivan Saveljic v Milos Nikolic | 2-6,6-7 |
| ITF Macedonia F2 | 2016/06/26 14:00 | Gabriel Donev v Milos Nikolic | 6-3,6-4 |
| ITF Macedonia F2 | 2016/06/25 14:00 | Luka Pavlovic v Milos Nikolic | 0-6,3-6 |
| ITF Macedonia F1 Qual | 2016/06/19 07:00 | Milos Nikolic v Goran Markovic | 3-6,2-6 |
| ITF Macedonia F1 Qual | 2016/06/18 08:00 | Milos Nikolic v Yuichiro Inui | 4-6,6-1,6-2 |
| ITF Greece F5 | 2016/04/17 08:30 | Milos Nikolic v Aaron Addison | 6-7,4-6 |