Ground: Hardcourt outdoor
| South Africa F2, Singles | 2014/06/06 09:30 | O'Brien, Dean v Scholtz, Nicolaas | 2-6,4-6 |
| South Africa F2, Singles | 2014/06/04 09:15 | O'Brien, Dean v Laubser, Brandon | 6-4,5-7,7-5 |
| ITF Mexico F3 | 2014/05/10 15:00 | O'Brien, Dean v King, Kevin | 3-6,2-6 |
| ITF Mexico F3 | 2014/05/09 15:00 | O'Brien, Dean v Estevez Maximiliano | 4-6,6-0,6-1 |
| ITF Mexico F3 | 2014/05/06 15:00 | Manuel Sanchez v O'Brien, Dean | 3-6,5-7 |
| ITF Mexico F2 | 2014/05/02 15:30 | Panta Herreros, Jorge Brian v O'Brien, Dean | 6-2,6-2 |
| Challenger - San Luis Potosí | 2014/04/15 21:45 | Arevalo-Gonzalez, Marcelo v O'Brien, Dean | 6-1,7-6 |
| Challenger San Luis Potosi Qual | 2014/04/13 18:25 | O'Brien, Dean v Krainik, Pavel | 6-4,6-4 |
| ITF South Africa F3 | 2014/06/10 09:10 | Benjamin Lock v Roelofse, Ruan | 6-7,1-6 |
| South Africa F2, Singles | 2014/06/05 08:00 | Scholtz, Nicolaas v Roelofse, Ruan | 3-6,6-3,7-6 |
| ITF South Africa F1 | 2014/05/27 09:40 | Cohen, Lance v Roelofse, Ruan | 4-6,6-7 |
| ITF Korea F1 | 2014/04/23 02:40 | Roelofse, Ruan v Kim, Cheong-Eui | 3-6,4-6 |
| Qatar F3, Singles | 2014/04/16 13:00 | Roelofse, Ruan v Golding, Oliver | 5-7,6-3,6-7 |
| Coupe Davis | 2014/04/06 09:30 | Roelofse, Ruan v Grigelis, Laurynas | 6-7,6-3,6-7,4-6 |
| ITF China F1 | 2014/03/05 03:30 | Chung, Hyeon v Roelofse, Ruan | 6-3,7-5 |