Stadium: Cancha 1 Round: 46 Ground: Clay
| Challenger Bogota Qual | 2016/11/05 15:00 | Dean O'Brien v Camilo Andres Erazo | 3-6,6-2,6-3 |
| Billie Jean King Cup | 2016/09/24 15:20 | Dean O'Brien v Ante Pavic | 2-6,3-6 |
| Challenger Izmir Qual | 2016/09/17 09:00 | Ruan Roelofse v Dean O'Brien | 6-0,6-3 |
| Challenger Aptos Qual | 2016/08/07 17:00 | Cameron Norrie v Dean O'Brien | 6-1,6-1 |
| Challenger Aptos Qual | 2016/08/06 20:10 | Michael Genender v Dean O'Brien | 3-6,2-6 |
| Challenger Dallas Qual | 2016/01/30 16:00 | Dean O'Brien v Clay Thompson | 4-6,2-6 |
| Challenger - Columbus | 2015/09/21 18:55 | Dean O'Brien v Sekou Bangoura | 3-6,1-6 |
| Challenger Columbus Qual | 2015/09/20 16:10 | Dean O'Brien v Herkko Pollanen | 6-3,6-4 |
| Challenger Bogota Qual | 2016/11/05 15:00 | Felipe Mantilla v Marcelo Zormann | 6-7,6-3,3-6 |
| Challenger Guayaquil Qual | 2016/10/29 20:40 | Michael Linzer v Marcelo Zormann | 6-4,6-2 |
| Challenger Guayaquil Qual | 2016/10/29 16:35 | Marcelo Zormann v Emilio Bowen | 6-0,6-2 |
| Challenger Lima Qual | 2016/10/22 16:55 | Pedro Sakamoto v Marcelo Zormann | 6-2,6-4 |
| Challenger Santiago 2 Qual | 2016/10/15 16:55 | Orlando Luz v Marcelo Zormann | 6-3,7-5 |
| Challenger Santiago 2 Qual | 2016/10/15 12:00 | Cristobal S-Corvalan v Marcelo Zormann | 4-6,5-7 |
| Challenger Buenos Aires 2 | 2016/10/11 19:40 | Marcelo Zormann v Pedro Sousa | 1-6,4-6 |
| Challenger Buenos Aires 2 Qual | 2016/10/10 15:05 | Marcelo Zormann v Fernando Romboli | 7-5,6-3 |