Round: 28 Ground: Hardcourt outdoor
| ITF Canada F8 | 2016/09/15 14:00 | Kaichi Uchida v Rhyne Williams | 2-6,2-6 |
| ITF Canada F8 | 2016/09/14 14:00 | Quinton Vega v Rhyne Williams | 1-6,2-6 |
| ITF Canada F8 | 2016/09/13 14:00 | Nicholas S. Hu v Rhyne Williams | 6-7,2-6 |
| ITF Canada F7 | 2016/09/09 16:00 | Frank Dancevic v Rhyne Williams | 6-4,6-2 |
| ITF Canada F7 | 2016/09/07 16:00 | Rhyne Williams v Carl Soderlund | 6-4,6-1 |
| ITF Canada F7 | 2016/09/05 19:35 | Riaan Du Toit v Rhyne Williams | 3-6,1-6 |
| ITF USA F27 | 2016/08/13 14:00 | Rhyne Williams v Christian Harrison | 7-6,3-6,4-6 |
| ITF USA F27 | 2016/08/12 14:00 | Wil Spencer v Rhyne Williams | 4-6,2-6 |
| ITF Canada F8 | 2016/09/15 14:00 | Takanyi Garanganga v Benjamin Sigouin | 6-2,5-7,3-6 |
| ITF Canada F8 | 2016/09/14 16:05 | Benjamin Sigouin v Ivan Endara | 6-4,6-2 |
| 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 |