Round: 25 Ground: Hardcourt outdoor
| 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 | David Volfson v Philip Bester | 7-6,1-6,6-3 |
| ITF Canada F7 | 2016/09/05 20:00 | David Volfson v Alex Rybakov | 6-7,6-2,6-2 |
| ITF Finland F3 | 2016/08/15 22:00 | David Volfson v Robbie Mudge | 6-4,4-6,4-6 |
| ITF Finland F3 Qual | 2016/08/14 22:00 | David Volfson v Jonathan Stenberg | 6-4,3-6,6-3 |
| ITF Finland F3 Qual | 2016/08/12 22:00 | David Volfson v Peter Sillanpaa | 6-1,6-1 |
| ITF Latvia F1 | 2016/08/03 07:00 | Claudio Fortuna v David Volfson | 6-3,6-3 |
| ITF Latvia F1 | 2016/08/02 07:00 | Harrison Lombe v David Volfson | 0-6,0-6 |
| 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 |
| ITF USA F20 | 2016/06/23 19:10 | Gavin Van Peperzeel v Raleigh Smith | 6-4,6-7,7-5 |