Round: 26 Ground: Hardcourt outdoor
| ITF Canada F8 | 2016/09/12 17:30 | Martin Beran v Francis Casey Alcantara | 7-6,4-6,4-6 |
| ITF Canada F7 - Qual. | 2016/09/04 15:00 | Francis Casey Alcantara v Egor Koleganov | 2-6,0-6 |
| ITF Canada F6 | 2016/09/01 17:00 | Francis Casey Alcantara v Tim Van Rijthoven | 6-7,2-6 |
| ITF Canada F6 | 2016/08/30 20:50 | Francis Casey Alcantara v Hans Hach Verdugo | 7-6,6-3 |
| ITF Hong Kong F3 | 2016/06/17 22:00 | Ming Chun Alan Sou v Francis Casey Alcantara | 1-6,2-6 |
| ITF Hong Kong F2 - Qual. | 2016/06/14 22:00 | Sami Reinwein v Francis Casey Alcantara | 6-3,6-2 |
| ITF Hong Kong F2 - Qual. | 2016/06/10 22:00 | Jonathan Gray v Francis Casey Alcantara | 2-6,4-6 |
| ITF Uzbekistan F4 | 2016/06/01 05:00 | Ti Chen v Francis Casey Alcantara | 7-6,3-6,6-3 |
| ITF Canada F8 | 2016/09/13 16:15 | David Volfson v Raleigh Smith | 5-7,1-6 |
| ITF Canada F7 | 2016/09/06 16:10 | Frank Dancevic v Raleigh Smith | 6-1,6-2 |
| ITF Canada F6 | 2016/08/31 18:30 | Raleigh Smith v Stefanos Tsitsipas | 6-7,5-7 |
| ITF Canada F6 | 2016/08/29 16:00 | Raleigh Smith v Antoine Leduc | 6-3,6-0 |
| Challenger Granby - Qual. | 2016/07/31 16:30 | James McGee v Raleigh Smith | 6-4,6-3 |
| Challenger Granby - Qual. | 2016/07/30 18:00 | Juan Carlos Aguilar v Raleigh Smith | 1-6,6-1,2-6 |
| ITF USA F22 | 2016/06/30 16:00 | Patrick Daciek v Raleigh Smith | 6-3,6-7,7-5 |
| ITF USA F22 | 2016/06/29 18:35 | Malik Bhatnagar v Raleigh Smith | 1-6,0-6 |