Round: 27 Ground: Hardcourt outdoor
| ITF USA F2 | 2016/01/14 18:00 | Raymond Sarmiento v Eric Quigley | 4-6,6-4,4-6 |
| Challenger Aptos | 2016/08/10 18:00 | Ernesto Escobedo v Raymond Sarmiento | 2-6,2-6 |
| Challenger Aptos | 2016/08/08 19:00 | Raymond Sarmiento v Lloyd Glasspool | 6-3,6-2 |
| 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 |
| Challenger Aptos | 2016/08/11 01:10 | Eric Quigley v Mackenzie McDonald | 5-7,6-4,6-2 |
| Challenger Aptos | 2016/08/08 19:30 | Eric Quigley v Christopher Eubanks | 6-2,6-1 |
| Challenger Aptos Qual | 2016/08/08 00:10 | Eric Quigley v Alexios Halebian | 6-4,7-6 |
| ATP Newport Qual | 2016/07/10 18:30 | Eric Quigley v Michal Przysiezny | 4-6,3-6 |
| ITF USA F23 | 2016/06/30 14:00 | Eric Quigley v Jared Hiltzik | 6-3,4-6,3-6 |
| ITF USA F23 | 2016/06/29 14:00 | Eric Quigley v Or Ram-Harel | 6-3,6-4 |
| ITF USA F18 | 2016/06/17 14:30 | Eric Quigley v Darian King | 6-7,1-6 |
| ITF USA F18 | 2016/06/16 14:00 | Eric Quigley v Reilly Opelka | 6-3,3-6,7-5 |