Stadium: CHRIS CAMMISA COURT Round: 45 Ground: Hardcourt outdoor
| 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 Greece F5 | 2016/04/24 07:00 | Jonny O'Mara v Lloyd Glasspool | 3-6,6-4,6-7 |
| ITF Greece F5 | 2016/04/23 07:00 | Lloyd Glasspool v Mick Lescure | 6-3,6-3 |
| ITF Greece F5 | 2016/04/22 08:45 | Daniel Cukierman v Lloyd Glasspool | 4-6,4-6 |
| ITF Greece F5 | 2016/04/21 10:15 | Hunter Callahan v Lloyd Glasspool | 6-7,2-6 |
| ITF Greece F5 | 2016/04/20 10:20 | Pavel Krainik v Lloyd Glasspool | 3-6,0-6 |
| ITF Germany F11 | 2016/08/14 12:00 | Hendrik Jebens v Marvin Rehberg | 6-2,3-6,3-6 |
| Challenger Segovia Qual | 2016/07/24 11:30 | Daniel Cox v Hendrik Jebens | 6-4,6-7,6-3 |
| Challenger Segovia Qual | 2016/07/23 12:00 | Saul V. Vicente v Hendrik Jebens | 4-6,1-6 |
| Challenger Recanati Qual | 2016/07/16 09:30 | Hendrik Jebens v Jesse Witten | 6-7,1-6 |
| ITF Germany F6 | 2016/07/04 10:00 | Hendrik Jebens v Johann Willems | 6-7,6-7 |
| ITF Germany F6 | 2016/07/03 12:00 | Hendrik Jebens v Chris Conrardy | 6-3,6-4 |
| ITF Germany F5 | 2016/06/30 12:00 | Marc Sieber v Hendrik Jebens | 6-4,6-4 |
| ITF Germany F5 | 2016/06/29 10:00 | Hendrik Jebens v Johann Willems | 5-7,7-5,6-1 |