Stadium: EVE ZIMMERMAN COURT Round: 46 Ground: Hardcourt outdoor
| 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 Winnipeg | 2016/07/11 23:00 | Bjorn Fratangelo v Lloyd Glasspool | 6-2,7-6 |
| Challenger Fairfield Qual | 2016/10/08 17:00 | Erik Crepaldi v Bernardo Saraiva | 6-2,6-2 |
| Challenger Stockton Qual | 2016/10/01 18:45 | Erik Crepaldi v Emilio Gomez | 4-6,1-6 |
| Challenger Tiburon Qual | 2016/09/25 17:00 | Michael Mmoh v Erik Crepaldi | 4-6,6-3,7-6 |
| Challenger Tiburon Qual | 2016/09/24 19:25 | Erik Crepaldi v Edoardo Eremin | 6-7,6-4,6-0 |
| Challenger Columbus Qual | 2016/09/19 15:00 | Erik Crepaldi v Gonzales Austin | 2-6,2-6 |
| Challenger Columbus Qual | 2016/09/18 14:00 | Erik Crepaldi v Ricky Medinilla | 6-1,6-2 |
| Challenger Columbus Qual | 2016/09/17 15:35 | Erik Crepaldi v Trey Yates | 6-3,7-6 |
| Challenger Cary | 2016/09/13 19:15 | Erik Crepaldi v Stefan Kozlov | 6-3,4-6,2-6 |