Round: 27 Ground: Hardcourt outdoor
| ITF USA F22 | 2016/06/30 18:00 | Winston Lin v Andrew Carter | 6-4,6-2 |
| ITF USA F22 | 2016/06/28 14:00 | Winston Lin v William Bushamuka | 6-4,4-6,6-4 |
| ITF USA F20 | 2016/06/24 00:00 | Marcus Fugate v Winston Lin | 6-3,7-5 |
| ITF USA F20 | 2016/06/22 22:30 | Sebastian Korda v Winston Lin | 2-6,4-6 |
| ITF USA F19 | 2016/06/17 21:00 | Winston Lin v Evan King | 4-6,1-6 |
| ITF USA F19 | 2016/06/16 15:00 | Winston Lin v Andrew Watson | 6-2,6-4 |
| ITF USA F19 | 2016/06/14 18:15 | Winston Lin v Quinton Vega | 7-6,6-3 |
| ITF Italy F32 | 2016/05/18 08:00 | Mate Delic v Winston Lin | 6-2,6-3 |
| ITF USA F22 | 2016/06/29 14:00 | Collin Johns v Connor Smith | 2-6,6-2,3-6 |
| ITF Netherlands F1 | 2016/06/17 09:00 | Yann Marti v Connor Smith | 6-4,6-1 |
| ITF Netherlands F1 | 2016/06/15 12:55 | Paul Monteban v Connor Smith | 0-6,2-6 |
| ITF Netherlands F1 | 2016/06/13 16:30 | Gijs Brouwer v Connor Smith | 2-6,1-6 |
| ITF China F9 | 2016/06/03 03:00 | Akira Santillan v Connor Smith | 6-3,6-3 |
| ITF China F9 | 2016/06/01 03:00 | Rigele Te v Connor Smith | 0-6,3-6 |
| ITF China F9 | 2016/05/30 06:00 | Xi Qi v Connor Smith | 4-6,2-6 |
| ITF China F8 | 2016/05/24 05:05 | Connor Smith v Kuan-Yi Lee | 7-5,1-6,2-6 |