Round: 44 Ground: Hardcourt outdoor
| ITF Canada F7 Qual | 2016/09/05 17:45 | Michael Lippens v Gary Kushnirovich | 3-6,6-7 |
| ITF Canada F7 Qual | 2016/09/04 14:00 | Kazuma Kawachi v Michael Lippens | 6-4,1-6,1-6 |
| ITF USA F22 Qual | 2016/06/25 16:30 | Dennis Uspensky v Michael Lippens | 6-7,6-2,6-1 |
| ITF USA F20 Qual | 2016/06/19 17:00 | Aryan Goveas v Michael Lippens | 6-3,6-3 |
| ITF USA F19 Qual | 2016/06/12 16:30 | Mauricio Resendiz Dominguez v Michael Lippens | 7-5,6-1 |
| ITF USA F19 Qual | 2016/06/11 17:00 | Eric Morris v Michael Lippens | 2-6,2-6 |
| ITF USA F16 | 2016/04/29 15:00 | Sean Burnette v Michael Lippens | 6-1,6-7,6-2 |
| ITF USA F15 Qual | 2016/04/25 15:00 | Juan Manuel Benitez Chavarriaga v Michael Lippens | 6-1,6-2 |
| 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 |
| ITF USA F24 Qual | 2016/07/16 15:30 | Brandon Donaldson v Eric Morris | 3-6,2-6 |
| ITF USA F18 | 2016/06/11 16:30 | Dominik Koepfer v Brandon Donaldson | 6-2,6-2 |
| ITF Canada F2 Qual | 2016/03/07 15:50 | Filip Peliwo v Brandon Donaldson | 6-1,6-2 |