Round: 27 Ground: Hardcourt outdoor
| Challenger Fairfield MD | 2016/10/10 22:10 | O'Brien/Roelofse v Farren/Giron | 6-2,7-6 |
| Challenger Stockton MD | 2016/10/05 17:00 | O'Brien/Roelofse v Arevalo/Klein | 6-7,4-6 |
| Challenger Izmir MD | 2016/09/19 11:00 | O'Brien/Roelofse v Hanfmann/Sieber | 6-7,3-6 |
| Challenger Istanbul MD | 2016/09/14 13:20 | O'Brien/Roelofse v Doumbia/Hemery | 3-6,6-0,8-10 |
| Challenger Istanbul MD | 2016/09/12 13:00 | O'Brien/Roelofse v Akkoyun/Yalcinkale | 6-1,6-2 |
| Challenger Aptos MD | 2016/08/11 23:00 | O'Brien/Roelofse v Scholtz/Vorster | 4-6,2-6 |
| Challenger Lexington MD | 2016/07/29 00:50 | Nedunchezhiyan/Ramanathan v O'Brien/Roelofse | 6-4,6-2 |
| Challenger Lexington MD | 2016/07/27 19:40 | Krueger/McDonald v O'Brien/Roelofse | 4-6,4-6 |
| Challenger Fairfield MD | 2016/10/11 22:35 | Caruso/Giannessi v Bangoura/Quigley | 6-3,5-7,4-10 |