Stadium: COURT 2 Round: 25 Ground: Hardcourt outdoor
| Challenger Tiburon | 2016/09/27 19:35 | Joris De Loore v Lloyd Glasspool | 6-2,7-6 |
| Challenger Tiburon Qual | 2016/09/26 17:00 | Dennis Nevolo v Lloyd Glasspool | 3-6,6-4,6-7 |
| Challenger Tiburon Qual | 2016/09/25 17:00 | Hubert Hurkacz v Lloyd Glasspool | 7-5,2-6,5-7 |
| Challenger Tiburon Qual | 2016/09/24 20:35 | Frederik Nielsen v Lloyd Glasspool | 7-5,1-6,4-6 |
| Challenger Columbus | 2016/09/21 15:00 | Hubert Hurkacz v Lloyd Glasspool | 6-4,7-5 |
| Challenger Aptos | 2016/08/08 19:00 | Raymond Sarmiento v Lloyd Glasspool | 6-3,6-2 |
| Challenger Winnipeg | 2016/07/11 23:00 | Bjorn Fratangelo v Lloyd Glasspool | 6-2,7-6 |
| Wimbledon Qual | 2016/06/20 16:35 | Lloyd Glasspool v Dennis Novikov | 2-6,5-7 |
| Challenger Tiburon Qual | 2016/09/25 19:55 | Greg Jones v Dennis Nevolo | 6-7,1-6 |
| Challenger Tiburon Qual | 2016/09/24 18:40 | Lorenzo Sonego v Greg Jones | 2-6,7-6,4-6 |
| Challenger Granby Qual | 2016/07/31 16:30 | Greg Jones v Erik Crepaldi | 6-2,4-6,5-7 |
| Challenger Granby Qual | 2016/07/30 18:15 | Greg Jones v Luis David Martinez | 6-3,6-1 |
| ITF Canada F4 | 2016/06/29 19:35 | Greg Jones v Peter Polansky | 3-6,0-6 |
| ITF Canada F3 | 2016/06/21 17:00 | Alexis Galarneau v Greg Jones | 6-4,3-6,6-3 |
| ITF USA F18 | 2016/06/14 14:55 | Greg Jones v Reilly Opelka | 6-7,6-7 |
| ITF USA F17 | 2016/06/09 15:15 | Greg Jones v Tennys Sandgren | 4-6,0-6 |