Round: 62 Ground: Clay
| ITF USA F25 Qual | 2016/07/23 15:00 | Jarryd Woog v Jonathan Chang | 4-6,1-6 |
| ITF USA F24 | 2016/07/22 17:00 | Rhyne Williams v Jonathan Chang | 6-4,6-2 |
| ITF USA F24 | 2016/07/21 16:35 | Jonathan Chang v Dominik Koepfer | 6-7,6-2,7-5 |
| ITF USA F24 | 2016/07/20 17:55 | Christopher Eubanks v Jonathan Chang | 2-6,3-6 |
| ITF USA F24 Qual | 2016/07/18 15:00 | Jonathan Chang v Andrew Watson | 6-2,7-6 |
| ITF USA F24 Qual | 2016/07/17 14:00 | Jonathan Chang v Brian Battistone | 7-5,7-5 |
| ITF USA F24 Qual | 2016/07/16 15:00 | Strong Kirchheimer v Jonathan Chang | 4-6,6-1,5-7 |
| ITF USA F23 Qual | 2016/06/27 13:30 | Arjun Kadhe v Jonathan Chang | 6-4,2-6,6-4 |
| 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 |
| ITF Macedonia F1 Qual | 2016/06/19 14:00 | Francesco Garzelli v Strahinja Rakic | 4-6,6-7 |
| ITF Serbia F8 | 2015/08/18 10:55 | Luka Ilic v Strahinja Rakic | 6-3,3-6,6-3 |