Stadium: Court 7 Round: 46 Ground: Hardcourt outdoor
| Challenger Charlottesville Qual | 2016/10/29 17:40 | Roy Smith v Aron Hiltzik | 4-6,2-6 |
| ITF Canada F9 Qual | 2016/09/23 15:15 | Brayden Schnur v Roy Smith | 7-5,6-3 |
| ITF Canada F9 Qual | 2016/09/22 15:30 | Roy Smith v Kaichi Uchida | 6-3,6-2 |
| ITF Canada F9 Qual | 2016/09/21 17:20 | Winston Lin v Roy Smith | 3-6,4-6 |
| ITF Canada F9 Qual | 2016/09/19 14:00 | Roy Smith v Andrew Ochotta | 6-3,6-3 |
| ITF Canada F9 Qual | 2016/09/18 16:00 | Damien Ghader v Roy Smith | 0-6,1-6 |
| ITF Canada F9 Qual | 2016/09/17 16:00 | Michel-Alexandre Fortin v Roy Smith | 4-6,2-6 |
| ITF Canada F8 Qual | 2016/09/11 13:00 | Roy Smith v Serge Becerra | 1-6,1-6 |
| Challenger Champaign Qual | 2016/11/13 19:05 | Luke Bambridge v Marcos Giron | 4-6,6-3,6-7 |
| Challenger Champaign Qual | 2016/11/12 21:10 | Luke Bambridge v Aleksandar Kovacevic | 2-6,7-5,6-2 |
| Challenger Knoxville Qual | 2016/11/07 15:00 | Yuki Bhambri v Luke Bambridge | 6-1,7-6 |
| Challenger Charlottesville Qual | 2016/10/30 15:50 | JC Aragone v Luke Bambridge | 4-6,7-5,6-4 |
| ITF USA F32 | 2016/10/23 17:00 | Luke Bambridge v Dominik Koepfer | 4-6,4-6 |
| ITF USA F32 | 2016/10/22 17:30 | Benjamin Lock v Luke Bambridge | 3-6,4-6 |
| ITF USA F32 | 2016/10/21 17:15 | Wil Spencer v Luke Bambridge | 7-5,6-7,4-6 |
| ITF USA F32 | 2016/10/20 15:00 | Tomas Stillman v Luke Bambridge | 6-7,4-6 |