Stadium: COURT 3 Round: 45 Ground: Hardcourt indoor
| Challenger Bogota Qual | 2016/11/06 15:00 | Dean O'Brien v Marcelo Zormann | 3-6,5-7 |
| 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 | 2016/09/19 16:25 | Mikelis Libietis v Hunter Tubert | 6-4,6-1 |
| Challenger Columbus Qual | 2016/09/18 19:15 | Hugo Di Feo v Hunter Tubert | 6-7,2-6 |
| Challenger Columbus Qual | 2016/09/17 19:15 | Hunter Tubert v Joe Salisbury | 6-2,7-5 |