Round: 26 Ground: Hardcourt outdoor
| ITF USA F9 Qual | 2016/02/28 14:00 | Sean Burnette v Hunter Callahan | 4-6,2-6 |
| ITF USA F9 Qual | 2016/02/27 15:00 | Lourenco Gasperini v Hunter Callahan | 4-6,0-6 |
| ITF USA F8 Qual | 2016/02/19 22:30 | Hunter Callahan v Alejandro Tabilo | 6-3,6-3 |
| ITF USA F7 | 2016/02/17 17:30 | Hunter Callahan v Junior Alexander Ore | 6-3,4-6,5-7 |
| ITF USA F7 Qual | 2016/02/15 17:00 | Tomas Barrios Vera v Hunter Callahan | 2-6,6-2,6-3 |
| ITF USA F7 Qual | 2016/02/12 19:00 | Federico Juan Aguilar v Hunter Callahan | 2-6,1-6 |
| ITF USA F5 | 2016/01/29 14:00 | Wil Spencer v Hunter Callahan | 6-0,6-3 |
| ITF USA F5 | 2016/01/26 16:30 | Hunter Callahan v Rowland Phillips | 4-6,6-4,6-1 |
| Challenger Drummondville Qual | 2016/03/13 21:30 | Lloyd Glasspool v Edward Corrie | 4-6,6-3,3-6 |
| ITF Canada F2 | 2016/03/13 17:00 | Lloyd Glasspool v Stefan Kozlov | 6-4,4-6,4-6 |
| ITF Canada F2 | 2016/03/12 16:00 | Felix Auger Aliassime v Lloyd Glasspool | 4-6,2-6 |
| ITF Canada F2 | 2016/03/11 16:00 | Lloyd Glasspool v Eric Quigley | 1-6,6-2,6-4 |
| ITF Canada F2 | 2016/03/09 17:30 | Omar Jasika v Lloyd Glasspool | 2-6,3-6 |
| ITF Canada F1 | 2016/03/02 15:00 | Alexios Halebian v Lloyd Glasspool | 7-6,7-6 |
| ITF Canada F1 | 2016/02/29 23:35 | Christian Harrison v Lloyd Glasspool | 6-7,3-6 |
| ITF Great Britain F3 | 2016/02/16 12:30 | Lloyd Glasspool v Daniel Cox | 6-3,2-6,6-7 |