| 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 Sarasota MD | 2016/04/14 18:40 | O'Brien/Roelofse v Baughman/Halebian | 7-5,6-4 |
| Challenger Champaign MD | 2015/11/19 19:45 | O'Hare/Salisbury v O'Brien/Roelofse | 6-3,7-6 |
| Challenger Knoxville MD | 2015/11/13 00:20 | Novikov/Quigley v O'Brien/Roelofse | 6-4,7-6 |
| Challenger Las Vegas MD | 2015/10/22 21:45 | O'Brien/Roelofse v Bester/Polansky | 6-3,2-6,11-9 |