Stadion: Court 7 Round: 45
| ITF - Südafrika F3 | 2014/06/11 09:15 | Dean O'Brien v Ruan Roelofse | 4-6,4-6 |
| Challenger - Aptos - Qualifikation | 2016/08/07 18:30 | Raymond Sarmiento v Ruan Roelofse | 6-3,6-2 |
| Challenger - Leon - Qualifikation | 2016/03/27 19:05 | Fabricio Neis v Ruan Roelofse | 6-3,6-2 |
| Challenger - San Luis Potosi - Qualifikation | 2016/03/19 18:05 | Ruan Roelofse v Facundo Mena | 6-7,4-6 |
| Challenger - Morelos - Qualifikation | 2016/02/14 17:20 | Ruan Roelofse v Gonzalo Escobar | 1-6,4-6 |
| Challenger - Morelos - Qualifikation | 2016/02/13 21:00 | Aitor Aramburu v Ruan Roelofse | 3-6,2-6 |
| Challenger - Santo Domingo - Qualifkation | 2016/02/07 20:30 | Ruan Roelofse v Gerard Granollers-Pujol | 7-6,4-6,4-6 |
| Challenger - Santo Domingo - Qualifkation | 2016/02/06 16:00 | Sebastian Serrano v Ruan Roelofse | 5-7,4-6 |
| Challenger - Columbus - Qualifikation | 2015/09/20 14:00 | Ruan Roelofse v Hugo Di Feo | 1-6,4-6 |
| Challenger - Aptos - Qualifikation | 2016/08/07 17:00 | Cameron Norrie v Dean O'Brien | 6-1,6-1 |
| Challenger - Aptos - Qualifikation | 2016/08/06 20:10 | Michael Genender v Dean O'Brien | 3-6,2-6 |
| Challenger - Dallas - Qualifikation | 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 - Qualifikation | 2015/09/20 16:10 | Dean O'Brien v Herkko Pollanen | 6-3,6-4 |
| ITF - Usbekistan F4 | 2015/06/10 06:25 | Temur Ismailov v Dean O'Brien | 6-2,6-1 |
| ITF - Usbekistan F4 | 2015/06/09 07:40 | Dean O'Brien v Pavel Tsoy | 6-3,6-4 |
| Challenger - Drummondville - Qualifikation | 2015/03/16 15:45 | Adam El Mihdawy v Dean O'Brien | 6-3,6-2 |