Round: 54 Ground: Hardcourt outdoor
| Challenger Fairfield Qual | 2016/10/09 18:20 | Lloyd Glasspool v Erik Crepaldi | 6-2,6-3 |
| Challenger Fairfield Qual | 2016/10/08 17:00 | Lloyd Glasspool v Hendrik Jebens | 6-3,6-7,7-6 |
| 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 Fairfield Qual | 2016/10/09 17:00 | Brandon Nakashima v Brydan Klein | 2-6,0-6 |
| Challenger Fairfield Qual | 2016/10/08 17:00 | Jan Choinski v Brydan Klein | 6-7,0-6 |
| Challenger Stockton | 2016/10/06 17:00 | Frank Dancevic v Brydan Klein | 6-4,6-4 |
| Challenger Stockton | 2016/10/04 17:00 | Brydan Klein v Quentin Halys | 2-6,6-4,6-1 |
| Challenger Stockton Qual | 2016/10/03 20:10 | Brydan Klein v Jan Choinski | 6-7,6-4,6-1 |
| Challenger Stockton Qual | 2016/10/02 17:00 | Brydan Klein v Andrew Carter | 6-1,6-3 |
| Challenger Stockton Qual | 2016/10/01 17:00 | Austin Krajicek v Brydan Klein | 5-7,6-2,2-6 |
| Challenger Tiburon Qual | 2016/09/26 17:00 | Matt Reid v Brydan Klein | 3-6,5-7 |