Round: 28 Ground: Hardcourt outdoor
| Challenger Tallahassee Qual | 2016/04/23 14:00 | Andrew Carter v Ryan Haviland | 6-4,6-7,6-0 |
| Challenger Savannah Qual | 2016/04/18 15:00 | Ryan Haviland v Roman Safiullin | 6-4,2-6,2-6 |
| Challenger Savannah Qual | 2016/04/17 18:50 | Connor Smith v Ryan Haviland | 4-6,6-4,3-6 |
| ITF USA F12 | 2016/04/09 16:00 | Ryan Haviland v Tennys Sandgren | 2-6,2-6 |
| ITF USA F12 | 2016/04/08 17:35 | Jan Choinski v Ryan Haviland | 1-6,2-6 |
| ITF USA F12 | 2016/04/07 16:05 | Ryan Haviland v Nicolas Meister | 6-4,6-4 |
| ITF USA F12 | 2016/04/05 14:00 | Nick Chappell v Ryan Haviland | 3-6,4-6 |
| Challenger Dallas Qual | 2016/01/31 17:35 | Alex Rybakov v Ryan Haviland | 3-6,6-7 |
| ITF USA F23 Qual | 2015/07/27 13:30 | Collin Johns v Paul Oosterbaan | 6-4,6-0 |
| ITF USA F23 Qual | 2015/07/26 13:30 | Paul Oosterbaan v Isaiah Strode | 7-5,6-2 |