Stadium: COURT 2 Round: 27 Ground: Hardcourt outdoor
| ITF USA F13 | 2016/04/15 20:00 | Philip Bester v Dennis Nevolo | 0-6,1-6 |
| Challenger Stockton Qual | 2016/10/02 18:20 | Eric Quigley v Dennis Nevolo | 2-6,4-6 |
| Challenger Stockton Qual | 2016/10/01 20:25 | Luke Bambridge v Dennis Nevolo | 3-6,3-6 |
| 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 19:55 | Greg Jones v Dennis Nevolo | 6-7,1-6 |
| Challenger Tiburon Qual | 2016/09/24 21:05 | Dennis Nevolo v Joe Salisbury | 3-6,6-3,6-1 |
| ITF USA F27 | 2016/08/08 17:45 | Ryan Shane v Dennis Nevolo | 7-5,6-3 |
| ITF USA F26 | 2016/08/02 17:20 | Jared Hiltzik v Dennis Nevolo | 3-6,6-2,7-6 |
| ITF USA F25 | 2016/07/27 16:30 | Connor Smith v Dennis Nevolo | 6-4,6-0 |
| Challenger Stockton Qual | 2016/10/02 17:50 | Mico Santiago v Philip Bester | 3-6,1-6 |
| Challenger Stockton Qual | 2016/10/01 20:55 | Philip Bester v Nils Langer | 6-3,7-6 |
| Challenger Columbus | 2016/09/20 16:50 | Tennys Sandgren v Philip Bester | 6-4,6-4 |
| Challenger Cary | 2016/09/15 18:45 | Philip Bester v Stefan Kozlov | 4-6,1-6 |
| Challenger Cary | 2016/09/13 16:00 | Philip Bester v Nicolas Meister | 7-5,6-3 |
| ITF Canada F7 | 2016/09/08 16:00 | David Volfson v Philip Bester | 7-6,1-6,6-3 |
| ITF Canada F7 | 2016/09/06 17:35 | Andrew Carter v Philip Bester | 3-6,2-6 |
| ITF Canada F6 | 2016/09/03 18:00 | Philip Bester v Brayden Schnur | 4-6,6-3,3-6 |