Round: 26 Ground: Hardcourt outdoor
| ITF Canada F8 | 2016/09/13 18:30 | Benjamin Sigouin v Konrad Zieba | 6-4,6-4 |
| Challenger Winnipeg | 2016/07/12 20:35 | Mitchell Krueger v Benjamin Sigouin | 6-0,6-4 |
| ITF Canada F2 | 2016/03/08 15:00 | Benjamin Sigouin v Eric Quigley | 7-6,2-6,3-6 |
| ITF Canada F1 Qual | 2016/02/28 15:00 | Jarryd Chaplin v Benjamin Sigouin | 7-6,3-6,7-6 |
| ITF Canada F1 Qual | 2016/02/27 15:00 | Alexis Galarneau v Benjamin Sigouin | 4-6,7-5,6-7 |
| ITF Canada F9 Qual | 2015/09/13 14:00 | Sami Reinwein v Benjamin Sigouin | 7-6,6-1 |
| ITF Canada F2 | 2015/03/11 16:00 | Filip Veger v Benjamin Sigouin | 6-3,6-4 |
| ITF Canada F2 Qual | 2015/03/08 13:00 | Benjamin Sigouin v Nicholas Reyes | 6-4,6-0 |
| 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 |
| Challenger Cali 2 Qual | 2016/07/03 19:50 | Luis Patino v Ivan Endara | 6-4,6-4 |
| ITF Colombia F3 | 2016/06/28 16:40 | Christopher Diaz-Figueroa v Ivan Endara | 4-6,6-3,6-3 |