Round: 25 Ground: Hardcourt indoor
| ITF Finland F3 | 2016/08/14 22:00 | Winston Lin v Eero Vasa | 6-7,6-1,3-6 |
| ITF Finland F2 | 2016/08/09 07:30 | Winston Lin v Matvey Khomentovskiy | 4-6,2-6 |
| ITF Finland F1 | 2016/08/04 13:00 | Rubin Statham v Winston Lin | 6-4,6-0 |
| ITF Finland F1 | 2016/08/03 10:30 | Patrik Brydolf v Winston Lin | 6-7,2-6 |
| ITF USA F22 | 2016/07/02 14:00 | Winston Lin v Kaichi Uchida | 2-6,6-7 |
| ITF USA F22 | 2016/07/01 16:10 | Winston Lin v Connor Smith | 6-3,6-4 |
| 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 F27 Qual | 2016/08/07 13:30 | Gonzalo Escobar v Roy Smith | 6-1,6-0 |
| ITF USA F27 Qual | 2016/08/06 13:30 | Roy Smith v Colin Markes | 6-3,6-4 |
| ITF USA F26 Qual | 2016/07/30 15:00 | Roy Smith v Alfredo Perez | 6-7,1-6 |
| ITF USA F25 Qual | 2016/07/24 13:15 | Roy Smith v Dragos Constantin Ignat | 6-7,1-6 |
| ITF USA F25 Qual | 2016/07/23 13:30 | Roy Smith v Jason Seidman | 6-1,6-1 |
| ITF USA F24 Qual | 2016/07/16 15:00 | Roy Smith v Andrew Watson | 2-6,1-6 |
| ITF USA F23 Qual | 2016/06/25 15:30 | Michael Riechmann v Roy Smith | 3-6,6-4,7-5 |
| ITF USA F20 Qual | 2016/06/20 17:00 | Roy Smith v Korey Lovett | 3-6,1-6 |