Round: 27 Ground: Hardcourt outdoor
| 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 |
| ITF USA F20 | 2016/06/23 19:10 | Gavin Van Peperzeel v Raleigh Smith | 6-4,6-7,7-5 |
| ITF USA F19 | 2016/06/15 18:20 | Gavin Van Peperzeel v Raleigh Smith | 6-3,6-1 |
| ITF Canada F6 | 2016/09/02 17:00 | Filip Peliwo v Stefanos Tsitsipas | 2-6,1-6 |
| ITF Canada F6 | 2016/08/31 18:10 | Filip Peliwo v Jonathan Chang | 6-2,6-4 |
| ITF Canada F6 | 2016/08/29 17:30 | Filip Peliwo v Aron Hiltzik | 6-3,3-6,6-3 |
| Challenger Granby Qual | 2016/08/01 15:00 | Emilio Gomez v Filip Peliwo | 6-4,6-4 |
| Challenger Granby Qual | 2016/07/31 18:40 | Washi Gervais v Filip Peliwo | 4-6,4-6 |
| ITF Canada F4 | 2016/07/01 00:00 | Riaan Du Toit v Filip Peliwo | 4-6,6-3,6-2 |
| ITF Canada F4 | 2016/06/29 17:00 | Gonzales Austin v Filip Peliwo | 6-4,3-6,4-6 |
| ITF Canada F3 | 2016/06/24 20:10 | Finn Tearney v Filip Peliwo | 7-5,7-5 |