| ITF Canada F9 Qual | 2016/09/22 17:15 | Adam El Mihdawy v Raleigh Smith | 3-6,6-4,6-2 |
| ITF Canada F9 Qual | 2016/09/21 15:20 | Hans Hach Verdugo v Raleigh Smith | 3-6,5-7 |
| ITF Canada F8 | 2016/09/15 16:50 | Raleigh Smith v Filip Peliwo | 4-6,3-6 |
| ITF Canada F8 | 2016/09/14 14:00 | Francis Casey Alcantara v Raleigh Smith | 4-6,4-6 |
| 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 |
| ITF Canada F9 Qual | 2016/09/21 15:50 | Lev Kazakov v Ivan Endara | 6-7,6-3,6-2 |
| ITF Canada F8 | 2016/09/14 16:05 | Benjamin Sigouin v Ivan Endara | 6-4,6-2 |
| ITF Canada F8 | 2016/09/13 19:05 | Juan Carlos Aguilar v Ivan Endara | 2-6,4-6 |
| ITF Canada F7 | 2016/09/11 15:30 | Frank Dancevic v Ivan Endara | 7-6,7-6 |
| ITF Canada F7 | 2016/09/10 16:30 | Alexander Ritschard v Ivan Endara | 7-6,4-6,3-6 |
| ITF Canada F7 | 2016/09/09 16:00 | Ivan Endara v David Volfson | 6-3,2-6,6-1 |
| ITF Canada F7 | 2016/09/08 16:00 | Ivan Endara v Manuel Sanchez | 4-6,6-4,6-2 |
| ITF Canada F7 | 2016/09/06 19:00 | Takanyi Garanganga v Ivan Endara | 6-2,2-6,1-6 |