Round: 25 Ground: Clay
| ITF Finland F1 | 2016/08/04 13:00 | Рубин Стейтъм 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 Каичи Учида | 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 Уилям Бушамука | 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 | Себастиан Корда v Winston Lin | 2-6,4-6 |
| ITF Finland F2 Qual | 2016/08/07 13:45 | Matvey Khomentovskiy v Флеминг Питърс | 6-3,6-4 |
| ITF Finland F2 Qual | 2016/08/06 10:00 | Matvey Khomentovskiy v Mauricio A-Guzman | 6-2,6-1 |
| ITF Latvia F1 | 2016/08/03 08:30 | Matvey Khomentovskiy v Riccardo Maiga | 5-7,0-6 |
| ITF Latvia F1 | 2016/08/02 09:45 | Мачей Райски v Matvey Khomentovskiy | 6-7,1-6 |
| ITF Latvia F1 | 2016/07/31 10:20 | Matvey Khomentovskiy v Tadas Tarasevicius | 6-4,6-4 |
| ITF Latvia F1 | 2016/07/31 07:00 | Matvey Khomentovskiy v Pelle Boerma | 6-1,6-1 |
| ITF Austria F4 | 2016/07/26 12:20 | Matvey Khomentovskiy v Florian Fallert | 5-7,3-6 |
| ITF Austria F4 Qual | 2016/07/24 08:00 | Matvey Khomentovskiy v Lawrence Bataljin | 3-6,6-1,6-4 |