Stadium: CHRIS CAMMISA COURT Round: 45 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 |
| ITF USA F30 | 2016/09/24 20:00 | Hendrik Jebens v Tristan Boyer | 1-6,1-6 |
| ITF USA F29 | 2016/09/19 18:30 | Gage Brymer v Hendrik Jebens | 6-2,6-3 |
| ITF USA F29 | 2016/09/18 18:00 | Jacob Brumm v Hendrik Jebens | 4-6,4-6 |
| ITF USA F29 | 2016/09/17 20:00 | Marcelo Tebet v Hendrik Jebens | 6-4,4-6,1-6 |
| ITF USA F29 | 2016/09/16 23:00 | Joaquin Marquez v Hendrik Jebens | 2-6,3-6 |
| ITF USA F28 | 2016/09/13 18:30 | Hendrik Jebens v Alexios Halebian | 6-7,6-4,2-6 |
| ITF USA F28 | 2016/09/12 17:00 | Hendrik Jebens v Marcelo Tebet | 7-5,6-3 |
| ITF USA F28 | 2016/09/10 16:00 | Hendrik Jebens v Jakob Amilon | 6-3,6-4 |