Round: 27 Ground: Hardcourt outdoor
| Challenger Istanbul MD | 2016/09/12 13:00 | O'Brien D / Roelofse R v Akkoyun U / Yalcinkale B | 6-1,6-2 |
| Challenger Aptos MD | 2016/08/11 23:00 | O'Brien D / Roelofse R v Scholtz N / Vorster T | 4-6,2-6 |
| Challenger Lexington MD | 2016/07/29 00:50 | Nedunchezhiyan J / Ramanathan R v O'Brien D / Roelofse R | 6-4,6-2 |
| Challenger Lexington MD | 2016/07/27 19:40 | Krueger M / Mcdonald M v O'Brien D / Roelofse R | 4-6,4-6 |
| ITF Uzbekistan F4 | 2015/06/12 10:00 | O'Brien D / Roelofse R v Fayziev S / Karimov J | 7-5,6-4 |
| ITF Uzbekistan F4 | 2015/06/11 11:20 | O'Brien D / Roelofse R v Duldaev D / Sultanov K | 3-6,6-0,10-7 |
| ITF South Africa F3 MD | 2014/06/13 10:45 | O'Brien D / Roelofse R v Scholtz N / Vorster T | 7-6,6-4 |
| ITF South Africa F3 MD | 2014/06/12 11:10 | O'Brien D / Roelofse R v Lock/Lock | 6-0,6-2 |
| Challenger Istanbul MD | 2016/09/13 14:15 | Bega A / Mertens Y v Doumbia S / Hemery C | 1-6,0-6 |