Round: 28 Ground: Hardcourt outdoor
| ITF USA F21 | 2016/06/24 16:10 | Ryan Haviland v Michael Mmoh | 4-6,6-4,6-4 |
| ITF USA F21 | 2016/06/23 16:55 | Ryan Haviland v Arjun Kadhe | 6-0,6-1 |
| ITF USA F21 | 2016/06/21 14:00 | Takanyi Garanganga v Ryan Haviland | 1-6,1-6 |
| ITF USA F18 | 2016/06/15 15:10 | Sekou Bangoura v Ryan Haviland | 3-6,6-3,7-5 |
| ITF USA F17 | 2016/06/08 15:00 | Ryan Haviland v Peter Polansky | 4-6,3-6 |
| 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 F21 | 2016/06/24 15:25 | Adam El Mihdawy v Paul Oosterbaan | 3-6,6-4,3-6 |
| ITF USA F21 | 2016/06/23 14:00 | Paul Oosterbaan v Sekou Bangoura | 7-6,6-4 |
| ITF USA F21 Qual | 2016/06/20 14:00 | Matic Spec v Paul Oosterbaan | 4-6,4-6 |
| ITF USA F21 Qual | 2016/06/19 14:00 | Jarryd Woog v Paul Oosterbaan | 4-6,3-6 |
| 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 |