Round: 44 Ground: Hardcourt indoor
| ITF Canada F9 Qual | 2016/09/18 14:00 | Riaan Du Toit v Nicholas Kamisar | 6-3,3-6,2-6 |
| ITF Canada F9 Qual | 2016/09/17 14:00 | Nicholas Kamisar v Drew Van Orderlain | 6-1,5-7,6-1 |
| ITF Canada F8 Qual | 2016/09/12 15:50 | Nicholas Kamisar v Nicholas S. Hu | 3-6,3-6 |
| ITF Canada F8 Qual | 2016/09/12 07:33 | Nicholas Kamisar v Nicholas S. Hu | 3-6,3-6 |
| ITF Canada F8 Qual | 2016/09/11 13:00 | Nicholas Kamisar v Taha Baadi | 6-4,6-2 |
| ITF Canada F5 Qual | 2016/07/02 19:30 | Justin Roberts v Nicholas Kamisar | 6-2,6-3 |
| ITF Canada F3 Qual | 2016/06/20 20:05 | Nicholas Kamisar v Raheel Manji | 6-4,1-6,5-7 |
| ITF Canada F5 Qual | 2015/07/19 20:00 | Roy Hobbs v Nicholas Kamisar | 3-6,6-2,0-6 |
| ITF Canada F9 Qual | 2016/09/18 16:00 | Brandon Donaldson v Lakshit Sood | 6-2,6-0 |
| ITF Canada F9 Qual | 2016/09/17 14:00 | Brandon Donaldson v Justin Lunn | 6-2,6-2 |
| ITF Canada F8 Qual | 2016/09/10 13:00 | Michael Lippens v Brandon Donaldson | 6-1,5-7,6-1 |
| ITF Canada F7 Qual | 2016/09/05 16:00 | Washi Gervais v Brandon Donaldson | 6-3,6-2 |
| ITF Canada F7 Qual | 2016/09/04 14:00 | Tom Dynka v Brandon Donaldson | 1-6,1-6 |
| ITF USA F26 Qual | 2016/07/31 16:00 | Brandon Donaldson v Tom Fawcett | 2-6,1-6 |
| ITF USA F26 Qual | 2016/07/30 15:30 | Brandon Donaldson v Drew Van Orderlain | 6-2,6-3 |
| ITF USA F25 Qual | 2016/07/23 13:30 | Mico Santiago v Brandon Donaldson | 6-2,6-2 |