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