Round: 44 Ground: Clay
| ITF Bosnia and Herzegovina F2 Qual | 2016/05/16 10:30 | Domagoj Biljesko v Shinnosuke Hiramatsu | 6-1,6-2 |
| ITF Serbia F7 Qual | 2016/09/10 10:00 | Petar Trendafilov v Domagoj Biljesko | 7-6,6-3 |
| ITF Serbia F6 | 2016/09/09 08:00 | Kristijan Mesaros v Domagoj Biljesko | 6-4,6-0 |
| ITF Serbia F6 | 2016/09/08 09:15 | Bogdan Bobrov v Domagoj Biljesko | 3-6,1-6 |
| ITF Serbia F6 | 2016/09/06 08:30 | Domagoj Biljesko v Dejan Katic | 6-0,6-3 |
| ITF Serbia F5 | 2016/08/16 10:05 | Nerman Fatic v Domagoj Biljesko | 6-4,7-6 |
| ITF Serbia F4 | 2016/08/10 07:30 | Christopher O'Connell v Domagoj Biljesko | 6-2,6-1 |
| ITF Serbia F4 Qual | 2016/08/08 07:30 | Domagoj Biljesko v Milos Dabic | 7-6,6-4 |
| ITF Serbia F3 | 2016/08/03 08:00 | Michael Linzer v Domagoj Biljesko | 6-0,6-1 |
| ITF Serbia F8 Qual | 2016/09/17 07:00 | Shinnosuke Hiramatsu v Christos Keisidis | 6-4,6-3 |
| ITF Serbia F7 Qual | 2016/09/10 10:00 | Shunsuke Wakita v Shinnosuke Hiramatsu | 1-6,7-5,6-3 |
| ITF Serbia F6 | 2016/09/04 07:30 | Luka Pavlovic v Shinnosuke Hiramatsu | 0-6,6-4,6-2 |
| ITF Serbia F5 Qual | 2016/08/14 07:30 | David Szintai v Shinnosuke Hiramatsu | 6-3,6-4 |
| ITF Serbia F4 Qual | 2016/08/07 09:30 | Goran Markovic v Shinnosuke Hiramatsu | 7-6,7-6 |
| ITF Serbia F4 Qual | 2016/08/06 06:30 | Aziz Kijametovic v Shinnosuke Hiramatsu | 4-6,6-3,3-6 |
| ITF Serbia F2 Qual | 2016/07/23 09:30 | Ioannis Stergiou v Shinnosuke Hiramatsu | 6-2,6-3 |
| ITF Serbia F1 Qual | 2016/07/18 13:00 | Shinnosuke Hiramatsu v Besir Durguti | 4-6,4-6 |