Round: 27 Ground: Hardcourt outdoor
| ITF Canada F8 | 2016/09/14 16:05 | Winston Lin v Serge Becerra | 5-7,6-1,6-0 |
| ITF Canada F8 | 2016/09/13 16:05 | Winston Lin v Хънтър Рийс | 6-7,6-3,6-4 |
| ITF Canada F7 | 2016/09/06 16:25 | Мартин Беран v Winston Lin | 7-6,7-5 |
| ITF Finland F3 | 2016/08/14 22:00 | Winston Lin v Еро Васа | 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 | 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 Canada F8 | 2016/09/14 16:35 | Муендуа Мбитхи v Egor Koleganov | 1-6,0-6 |
| ITF Canada F8 | 2016/09/13 14:00 | Egor Koleganov v Мануел Санчес | 1-6,6-3,7-6 |
| ITF Canada F8 Qual | 2016/09/12 14:00 | Николас Байбел v Egor Koleganov | 1-6,3-6 |
| ITF Canada F8 Qual | 2016/09/11 13:00 | Egor Koleganov v Daniel Fainblum | 6-4,6-4 |
| ITF Canada F8 Qual | 2016/09/10 13:00 | Egor Koleganov v Том Динка | 6-2,6-2 |
| ITF Canada F7 Qual | 2016/09/05 16:00 | Egor Koleganov v Александър Ритшард | 6-3,4-6,2-6 |
| ITF Canada F7 Qual | 2016/09/04 15:00 | Франсис Кейси Алкантара v Egor Koleganov | 2-6,0-6 |
| ITF Canada F7 Qual | 2016/09/04 13:00 | Egor Koleganov v Себастиан Запата | 6-0,6-2 |