Round: 25 Ground: Hardcourt outdoor
| ITF Great Britain F2 | 2016/02/11 10:00 | Raymond Sarmiento v Lloyd Glasspool | 7-6,6-7,3-6 |
| Challenger Aptos Qual | 2016/08/07 18:30 | Raymond Sarmiento v Ruan Roelofse | 6-3,6-2 |
| Challenger Aptos Qual | 2016/08/06 19:35 | Raymond Sarmiento v Bernardo Saraiva | 6-1,6-2 |
| Challenger Granby Qual | 2016/08/01 15:00 | Raymond Sarmiento v Edward Corrie | 6-7,6-4,0-6 |
| Challenger Granby Qual | 2016/07/31 16:30 | Dayne Kelly v Raymond Sarmiento | 4-6,4-6 |
| Challenger Granby Qual | 2016/07/30 16:00 | Raymond Sarmiento v Nicaise Muamba | 6-3,6-4 |
| ITF Canada F4 | 2016/07/03 20:00 | Raymond Sarmiento v Peter Polansky | 2-6,4-6 |
| ITF Canada F4 | 2016/07/02 20:00 | Raymond Sarmiento v Sebastien Boltz | 6-3,6-1 |
| ITF Canada F4 | 2016/07/01 18:00 | Raymond Sarmiento v Riaan Du Toit | 6-2,6-3 |
| 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 Greece F4 | 2016/04/17 09:05 | Yannick Mertens v Lloyd Glasspool | 6-2,7-5 |