Round: 62 Ground: Clay
| ITF Canada F7 | 2016/09/09 16:00 | Alexander Ritschard v Jonathan Chang | 6-1,6-0 |
| ITF Canada F7 | 2016/09/08 16:00 | Martin Beran v Jonathan Chang | 5-7,2-6 |
| ITF Canada F7 | 2016/09/06 14:30 | Jonathan Chang v Kaichi Uchida | 6-4,3-6,6-2 |
| ITF Canada F7 Qual | 2016/09/05 16:00 | Jonathan Chang v Nicaise Muamba | 6-4,6-1 |
| ITF Canada F7 Qual | 2016/09/04 14:00 | Jonathan Chang v Chih Chi Huang | 6-2,6-0 |
| ITF Canada F6 | 2016/08/31 18:10 | Filip Peliwo v Jonathan Chang | 6-2,6-4 |
| ITF Canada F6 | 2016/08/29 16:00 | Michael Genender v Jonathan Chang | 3-6,4-6 |
| ITF USA F25 Qual | 2016/07/23 15:00 | Jarryd Woog v Jonathan Chang | 4-6,1-6 |
| ITF Serbia F2 | 2016/07/28 12:45 | Kristijan Mesaros v Strahinja Rakic | 6-3,1-6,6-2 |
| ITF Serbia F2 | 2016/07/26 10:00 | Strahinja Rakic v Goran Markovic | 6-3,0-6,7-6 |
| ITF Serbia F1 Qual | 2016/07/16 10:00 | Strahinja Rakic v Aitor Aramburu | 6-1,7-6 |
| ITF Macedonia F1 | 2016/07/05 10:10 | Strahinja Rakic v Lenny Hampel | 1-6,2-6 |
| ITF Macedonia F1 | 2016/07/04 10:50 | Domagoj Biljesko v Strahinja Rakic | 3-6,4-6 |
| ITF Macedonia F2 | 2016/06/26 12:00 | Christian Hirschmueller v Strahinja Rakic | 6-4,6-1 |
| ITF Macedonia F1 | 2016/06/21 14:00 | Strahinja Rakic v Giorgio Ricca | 6-4,3-6,2-6 |
| ITF Macedonia F1 Qual | 2016/06/20 08:00 | Strahinja Rakic v Keisuke Numajiri | 6-3,6-2 |