Round: 60 Ground: Clay
| ITF USA F8 Qual | 2016/02/20 16:30 | Sylvester Emmanuel v Webb, Dane | 2-6,7-6,1-6 |
| ITF USA F8 Qual | 2016/02/19 16:30 | Webb, Dane v Achondo, Gonzalo | 7-5,7-5 |
| Challenger Dallas Qual | 2016/01/30 19:10 | Webb, Dane v Estevez Maximiliano | 7-5,6-3 |
| ITF Dominican Republic F3 | 2015/12/14 13:30 | Webb, Dane v Reese, Hunter | 5-7,6-3,6-7 |
| ITF Dominican Republic F3 | 2015/12/13 14:00 | Merino, Alexander v Webb, Dane | 3-6,2-6 |
| ITF Dominican Republic F2 | 2015/12/08 18:00 | Goncalo Oliveira v Webb, Dane | 6-4,7-5 |
| ITF Dominican Republic F2 | 2015/12/07 14:00 | Kopinski, Tim v Webb, Dane | 6-7,6-7 |
| ITF Dominican Republic F2 | 2015/12/06 15:00 | Webb, Dane v Matveyko, Nikita | 6-4,6-4 |
| ITF USA F8 Qual | 2016/02/19 16:30 | Holt, Bradley v Montero, Jorge | 1-6,1-6 |
| ITF USA F7 Qual | 2016/02/14 17:00 | Montero, Jorge v Benitez Chavarriaga, Juan Manuel | 1-6,1-6 |
| ITF USA F7 Qual | 2016/02/13 18:00 | Montero, Jorge v Ghinda, Iancu-Lustinian | 6-0,6-2 |
| ITF USA F7 Qual | 2016/02/12 17:00 | Montero, Jorge v August Holmgren | 6-3,6-2 |
| ITF Chile F8 | 2015/12/02 14:00 | Tomas Barrios Vera v Montero, Jorge | 6-3,6-2 |
| ITF Chile F8 | 2015/11/30 17:00 | Montero, Jorge v Gonzalo Villanueva | 7-6,6-3 |
| ITF Colombia F9 | 2015/11/05 15:00 | Montero, Jorge v Manuel Sanchez | 6-3,4-6,2-6 |
| ITF Colombia F8 | 2015/10/29 15:00 | Tomas Barrios Vera v Montero, Jorge | 6-3,6-2 |