Round: 54 Ground: Clay
| Challenger Sarasota Qual | 2016/04/10 18:10 | Deiton Baughman v Tomas Lipovsek Puches | 2-6,2-6 |
| Challenger Savannah Qual | 2016/04/17 15:00 | Tomas Lipovsek Puches v Rubin Statham | 6-4,1-6,6-2 |
| Challenger Sarasota | 2016/04/15 15:00 | Bjorn Fratangelo v Tomas Lipovsek Puches | 6-4,6-1 |
| Challenger Sarasota | 2016/04/14 15:00 | Tomas Lipovsek Puches v Guido Andreozzi | 7-6,1-6,6-2 |
| Challenger Sarasota | 2016/04/12 15:00 | Peter Nagy v Tomas Lipovsek Puches | 6-3,2-6,3-6 |
| Challenger Sarasota Qual | 2016/04/10 18:10 | Deiton Baughman v Tomas Lipovsek Puches | 2-6,2-6 |
| Challenger Sarasota Qual | 2016/04/09 14:00 | Collin Johns v Tomas Lipovsek Puches | 3-6,0-6 |
| ITF Argentina F3 | 2016/03/19 18:00 | Pedro Sakamoto v Tomas Lipovsek Puches | 4-6,6-2,1-6 |
| ITF Argentina F3 | 2016/03/19 12:00 | Tomas Lipovsek Puches v Michael Linzer | 1-6,6-3,7-6 |
| Challenger Savannah Qual | 2016/04/17 17:10 | Marc Polmans v Deiton Baughman | 4-6,6-7 |
| Challenger Sarasota Qual | 2016/04/10 18:10 | Deiton Baughman v Tomas Lipovsek Puches | 2-6,2-6 |
| Challenger Sarasota Qual | 2016/04/09 14:00 | Juan Sebastian Gomez v Deiton Baughman | 6-7,2-6 |
| ITF USA F11 | 2016/03/22 17:00 | Orlando Luz v Deiton Baughman | 6-4,6-0 |
| Challenger Drummondville | 2016/03/15 18:55 | Edward Corrie v Deiton Baughman | 6-2,6-4 |
| ITF Canada F2 | 2016/03/09 15:00 | Tim Van Rijthoven v Deiton Baughman | 6-7,6-1,6-4 |
| ITF Canada F1 | 2016/03/04 20:00 | Edward Corrie v Deiton Baughman | 5-7,6-2,6-4 |
| ITF Canada F1 | 2016/03/03 15:30 | Alejandro Tabilo v Deiton Baughman | 5-7,6-1,4-6 |