Stadium: ESTADIO Round: 27 Ground: Hardcourt outdoor
| Challenger Columbus | 2016/09/24 15:30 | Benjamin Becker v John-Patrick Smith | 6-4,1-6,7-5 |
| Challenger Monterrey | 2016/10/12 19:35 | Alessandro Bega v John-Patrick Smith | 2-6,6-3,0-6 |
| Challenger Monterrey | 2016/10/11 17:00 | John-Patrick Smith v Mauricio Astorga | 6-3,6-2 |
| Challenger Tiburon | 2016/09/29 19:55 | Frances Tiafoe v John-Patrick Smith | 6-3,6-3 |
| Challenger Tiburon | 2016/09/27 17:00 | John-Patrick Smith v Marcelo Arevalo | 6-3,3-6,6-3 |
| Challenger Columbus | 2016/09/24 15:30 | Benjamin Becker v John-Patrick Smith | 6-4,1-6,7-5 |
| Challenger Columbus | 2016/09/23 17:50 | Sekou Bangoura v John-Patrick Smith | 3-6,6-3,3-6 |
| Challenger Columbus | 2016/09/22 15:00 | Hubert Hurkacz v John-Patrick Smith | 2-6,3-6 |
| Challenger Columbus | 2016/09/20 14:00 | John-Patrick Smith v Marcelo Arevalo | 6-1,6-1 |
| Challenger Monterrey | 2016/10/12 19:30 | Emilio Gomez v Benjamin Becker | 3-6,6-7 |
| Challenger Tiburon | 2016/09/27 22:00 | Benjamin Becker v Tommy Paul | 7-6,6-2 |
| Challenger Columbus | 2016/09/25 18:00 | Benjamin Becker v Mikael Torpegaard | 4-6,6-1,2-6 |
| Challenger Columbus | 2016/09/24 15:30 | Benjamin Becker v John-Patrick Smith | 6-4,1-6,7-5 |
| Challenger Columbus | 2016/09/23 16:00 | Benjamin Becker v Mikelis Libietis | 4-6,6-1,7-6 |
| Challenger Columbus | 2016/09/22 16:40 | Benjamin Becker v Sam Groth | 6-3,6-2 |
| Challenger Columbus | 2016/09/20 20:45 | Benjamin Becker v Eric Quigley | 7-5,6-4 |
| US Open 2016 | 2016/08/30 15:00 | Kei Nishikori v Benjamin Becker | 6-1,6-1,3-6,6-3 |