Round: 25 Ground: Clay
| Challenger Sarasota Qual | 2016/04/09 17:35 | Roman Safiullin v Raleigh Smith | 6-1,6-3 |
| ITF USA F11 Qual | 2016/03/21 19:10 | Hubert Hurkacz v Raleigh Smith | 6-2,6-1 |
| ITF USA F10 Qual | 2016/03/12 17:00 | Raleigh Smith v Jared Thompkins | 6-2,6-0 |
| ITF USA F8 | 2016/02/23 17:00 | Raleigh Smith v Andrea Collarini | 4-6,4-6 |
| ITF USA F8 Qual | 2016/02/22 17:00 | Raleigh Smith v Roberto Quiroz | 0-6,4-6 |
| ITF USA F8 Qual | 2016/02/21 16:00 | Juan Sebastian Gomez v Raleigh Smith | 2-6,6-1,6-7 |
| ITF USA F8 Qual | 2016/02/20 17:30 | Abhijeet Joshi v Raleigh Smith | 3-6,1-6 |
| ITF USA F8 Qual | 2016/02/19 18:30 | Raleigh Smith v Jose Daniel Bendeck | 6-3,6-3 |
| ITF USA F13 | 2016/04/16 19:05 | Eric Quigley v Dennis Nevolo | 6-3,6-1 |
| ITF USA F13 | 2016/04/15 20:00 | Philip Bester v Dennis Nevolo | 0-6,1-6 |
| ITF USA F13 | 2016/04/14 17:05 | Dennis Nevolo v Nicolaas Scholtz | 6-4,6-2 |
| ITF USA F13 | 2016/04/13 22:55 | Dennis Nevolo v Mico Santiago | 6-2,6-4 |
| ITF USA F12 | 2016/04/09 18:00 | Dennis Nevolo v Denis Shapovalov | 3-6,4-6 |
| ITF USA F12 | 2016/04/08 17:30 | Christian Lindell v Dennis Nevolo | 2-6,4-6 |
| ITF USA F12 | 2016/04/07 19:35 | Sebastian Fanselow v Dennis Nevolo | 5-7,4-6 |
| ITF USA F12 | 2016/04/05 15:35 | Dennis Nevolo v Evan King | 6-2,6-1 |