Round: 46 Ground: Hardcourt outdoor
| Challenger Winnipeg | 2016/07/14 19:45 | Peter Polansky v James McGee | 6-4,6-1 |
| Challenger Winnipeg | 2016/07/12 19:35 | Nicolas Meister v James McGee | 2-6,2-6 |
| Challenger Winnipeg Qual | 2016/07/10 16:45 | James McGee v Luke Bambridge | 6-4,6-4 |
| Challenger Milan Qual | 2016/06/19 09:30 | James McGee v Nicolas Jarry | 4-6,6-7 |
| Challenger Milan Qual | 2016/06/18 09:05 | James McGee v Eduardo Dischinger | 6-2,6-1 |
| Challenger Blois Qual | 2016/06/13 14:00 | James McGee v Juan Pablo Paz | 4-6,0-6 |
| Challenger Blois Qual | 2016/06/13 08:00 | James McGee v Bastian Malla | 6-3,6-3 |
| Challenger Mestre Qual | 2016/05/16 10:00 | James McGee v Daniel Masur | 3-6,3-6 |
| 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 Mexico F3 | 2016/05/20 15:00 | Raleigh Smith v Roberto Quiroz | 5-7,6-7 |
| ITF Mexico F3 | 2016/05/18 15:30 | Raleigh Smith v Mauricio Astorga | 6-4,7-6 |
| ITF Mexico F3 | 2016/05/17 15:00 | Federico Zeballos v Raleigh Smith | 6-7,7-5,4-6 |