Round: 60 Ground: Clay
| Challenger Tallahassee Qual | 2016/04/23 16:50 | Jared Thompkins v Blake Mott | 3-6,1-6 |
| ITF USA F14 | 2016/04/17 14:30 | Juan Manuel Benitez Chavarriaga v Jared Thompkins | 6-0,6-2 |
| ITF USA F11 Qual | 2016/03/20 16:00 | Jared Thompkins v Tyler Hochwalt | 5-7,1-6 |
| ITF USA F10 Qual | 2016/03/12 17:00 | Raleigh Smith v Jared Thompkins | 6-2,6-0 |
| ITF USA F9 Qual | 2016/02/26 16:00 | Evan Bynoe v Jared Thompkins | 7-6,6-1 |
| ITF USA F8 Qual | 2016/02/19 20:00 | Piotr Zbroja v Jared Thompkins | 6-4,3-6,6-2 |
| ITF USA F2 Qual | 2016/01/09 18:00 | Alejandro Tabilo v Jared Thompkins | 6-1,6-1 |
| ITF USA F33 Qual | 2015/11/14 16:30 | Bruno Savi v Jared Thompkins | 6-3,6-2 |
| ITF USA F15 Qual | 2016/04/22 20:30 | Mason Beiler v William Genesen | 2-6,2-6 |
| ITF USA F14 | 2016/04/20 14:00 | Denis Shapovalov v Mason Beiler | 6-3,6-4 |
| ITF USA F14 | 2016/04/18 17:00 | Mason Beiler v Joel Vincent Link | 6-2,7-5 |
| ITF USA F14 | 2016/04/18 13:30 | Mason Beiler v Tyler Mercier | 6-3,6-1 |
| ITF USA F14 | 2016/04/17 17:00 | Antoine Leduc v Mason Beiler | 2-6,0-6 |
| ITF USA F28 | 2015/09/26 18:00 | Patrick Daciek v Mason Beiler | 2-6,2-6 |
| ITF USA F28 | 2015/09/25 16:00 | Mason Beiler v Matthew Tsolakyan | 7-6,7-5 |
| ITF USA F26 Qual | 2015/09/12 16:00 | Mason Beiler v William Genesen | 3-6,6-4,3-6 |