Round: 26 Ground: Hardcourt outdoor
| Challenger Granby Qual | 2016/07/31 16:30 | James McGee v Raleigh Smith | 6-4,6-3 |
| Challenger Granby Qual | 2016/07/30 18:00 | Juan Carlos Aguilar v Raleigh Smith | 1-6,6-1,2-6 |
| ITF USA F22 | 2016/06/30 16:00 | Patrick Daciek v Raleigh Smith | 6-3,6-7,7-5 |
| ITF USA F22 | 2016/06/29 18:35 | Malik Bhatnagar v Raleigh Smith | 1-6,0-6 |
| ITF USA F20 | 2016/06/23 19:10 | Gavin Van Peperzeel v Raleigh Smith | 6-4,6-7,7-5 |
| ITF USA F19 | 2016/06/15 18:20 | Gavin Van Peperzeel v Raleigh Smith | 6-3,6-1 |
| ITF Mexico F3 | 2016/05/20 15:00 | Raleigh Smith v Roberto Quiroz | 5-7,6-7 |
| ITF Mexico F3 | 2016/05/18 15:30 | Raleigh Smith v Mauricio Astorga | 6-4,7-6 |
| ITF Egypt F21 | 2016/08/24 18:15 | Christopher Diaz-Figueroa v Stefan Skadarka | 6-7,2-6 |
| ITF Egypt F20 | 2016/08/18 17:25 | Issam Haitham Taweel v Christopher Diaz-Figueroa | 7-6,7-5 |
| ITF Egypt F19 | 2016/08/11 16:00 | Farris Fathi Gosea v Christopher Diaz-Figueroa | 7-6,6-4 |
| ITF Egypt F19 | 2016/08/10 17:25 | Hugo Largo v Christopher Diaz-Figueroa | 4-6,4-6 |
| Davis Cup | 2016/07/17 16:00 | Christopher Diaz-Figueroa v Martin Cuevas | 3-6,6-1,3-6,6-4,6-2 |
| Davis Cup | 2016/07/15 16:00 | Christopher Diaz-Figueroa v Rodrigo Arus | 7-5,6-2,6-4 |
| Challenger Cali 2 | 2016/07/05 17:55 | Giovanni Lapentti v Christopher Diaz-Figueroa | 7-5,7-6 |
| ITF Colombia F3 | 2016/06/30 16:00 | Christopher Diaz-Figueroa v Roberto Quiroz | 4-6,2-6 |