Round: 26 Ground: Clay
| ITF USA F22 | 2016/07/01 16:10 | Lin, Winston v Smith, Connor | 6-3,6-4 |
| ITF USA F31 | 2016/10/11 15:00 | Lenz, Julian v Lin, Winston | 3-6,6-4,2-6 |
| ITF Canada F9 Qual | 2016/09/21 17:20 | Lin, Winston v Smith, Roy | 3-6,4-6 |
| ITF Canada F8 | 2016/09/15 15:55 | Lin, Winston v Koleganov, Egor | 6-4,6-2 |
| ITF Canada F8 | 2016/09/14 16:05 | Lin, Winston v Becerra Jeria, Serge | 5-7,6-1,6-0 |
| ITF Canada F8 | 2016/09/13 16:05 | Lin, Winston v Reese, Hunter | 6-7,6-3,6-4 |
| Canada F7, Singles | 2016/09/06 16:25 | Beran, Martin v Lin, Winston | 7-6,7-5 |
| ITF Finland F3 | 2016/08/14 22:00 | Lin, Winston v Eero Vasa | 6-7,6-1,3-6 |
| ITF Finland F2 | 2016/08/09 07:30 | Lin, Winston v Khomentovskiy, Matvey | 4-6,2-6 |
| ITF USA F31 | 2016/10/11 17:50 | Rutledge, Eric v Smith, Connor | 0-6,4-6 |
| ITF Israel F13 | 2016/09/20 06:30 | Michelevitz, Guy v Smith, Connor | 4-6,4-6 |
| ITF Israel F12 | 2016/09/18 07:00 | Pauffley, Neil v Smith, Connor | 1-6,0-6 |
| ITF Israel F12 | 2016/09/17 07:00 | Smith, Connor v Song, Evan | 6-4,6-4 |
| ITF Israel F12 | 2016/09/16 07:00 | Kanar, Jonathan v Smith, Connor | 3-6,3-6 |
| ITF Israel F12 | 2016/09/15 07:00 | Webb, Dane v Smith, Connor | 1-6,1-6 |
| ITF Israel F12 | 2016/09/13 08:20 | Thomas, Danny v Smith, Connor | 6-3,5-7,3-6 |
| ITF Israel F11 | 2016/09/10 07:00 | Jankovits, Yannick v Smith, Connor | 6-7,3-6 |