Stadium: COURT 2 Round: 26 Ground: Hardcourt outdoor
| Challenger Stockton Qual | 2016/10/01 19:30 | Mico Santiago v Ross Watson | 6-2,6-1 |
| ITF USA F25 Qual | 2016/07/25 16:50 | Mico Santiago v Grayson M. Goldin | 1-6,2-6 |
| ITF USA F25 Qual | 2016/07/24 13:15 | Mico Santiago v Warren Race | 6-1,6-0 |
| ITF USA F25 Qual | 2016/07/23 13:30 | Mico Santiago v Brandon Donaldson | 6-2,6-2 |
| ITF USA F23 | 2016/06/30 15:35 | Mico Santiago v Clay Thompson | 3-6,6-3,2-6 |
| ITF USA F23 | 2016/06/29 16:00 | Mico Santiago v Jason Legall | 6-4,6-2 |
| ITF USA F21 | 2016/06/23 16:25 | Tennys Sandgren v Mico Santiago | 6-1,6-2 |
| ITF USA F21 | 2016/06/22 14:00 | Nathaniel Lammons v Mico Santiago | 2-6,2-6 |
| 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 |
| ITF Canada F6 | 2016/09/02 18:15 | Philip Bester v Gonzales Austin | 7-5,6-3 |