Round: 28 Ground: Hardcourt outdoor
| ITF USA F27 | 2016/08/08 18:45 | Christian Harrison v Connor Smith | 6-3,7-5 |
| ITF USA F26 | 2016/08/03 16:00 | Connor Smith v Alfredo Perez | 6-2,4-6,1-6 |
| ITF USA F25 | 2016/07/29 14:00 | Connor Smith v Tennys Sandgren | 3-6,0-6 |
| ITF USA F25 | 2016/07/28 14:00 | Connor Smith v Roberto Quiroz | 6-1,6-4 |
| ITF USA F25 | 2016/07/27 16:30 | Connor Smith v Dennis Nevolo | 6-4,6-0 |
| Challenger Cali 2 | 2016/07/05 16:30 | Erik Crepaldi v Connor Smith | 7-6,6-2 |
| ITF USA F22 | 2016/07/01 16:10 | Winston Lin v Connor Smith | 6-3,6-4 |
| ITF USA F22 | 2016/06/29 14:00 | Collin Johns v Connor Smith | 2-6,6-2,3-6 |
| ITF Canada F5 | 2016/07/07 23:00 | Sebastien Boltz v Evan Song | 6-2,6-2 |
| ITF Canada F5 | 2016/07/05 20:35 | Daniel Cukierman v Evan Song | 4-6,6-3,4-6 |
| ITF Canada F4 | 2016/06/30 19:55 | Blake Mott v Evan Song | 6-3,6-1 |
| ITF Canada F4 | 2016/06/28 17:00 | Evan Song v Ben Mclachlan | 7-5,6-4 |
| ITF Japan F7 | 2016/06/07 01:00 | Koichi Sano v Evan Song | 2-6,7-5,6-4 |
| ITF Japan F6 | 2016/06/01 01:00 | Evan Song v Shuichi Sekiguchi | 3-6,1-6 |
| ITF Japan F6 | 2016/05/31 01:00 | Masaki Sasai v Evan Song | 1-6,0-6 |
| ITF China F8 | 2016/05/26 03:00 | Evan Song v Filip Peliwo | 2-6,3-6 |