Ground: Hardcourt indoor
| ITF USA F28 | 2014/10/15 18:30 | Adam El Mihdawy v Dean O'Brien | 6-3,7-6 |
| ITF Colombia F5 | 2014/09/11 15:00 | Dean O'Brien v Fabiano De Paula | 4-6,3-6 |
| ITF Colombia F5 | 2014/09/10 16:35 | Dean O'Brien v Pedro Bernardi | 7-6,6-4 |
| ITF Colombia F4 | 2014/08/25 16:00 | Dean O'Brien v Fabiano De Paula | 6-7,3-6 |
| ITF France F11 | 2014/06/18 08:00 | Nils Langer v Dean O'Brien | 6-4,6-2 |
| ITF South Africa F3 | 2014/06/11 09:15 | Dean O'Brien v Ruan Roelofse | 4-6,4-6 |
| ITF South Africa F2 | 2014/06/06 09:30 | Dean O'Brien v Nicolaas Scholtz | 2-6,4-6 |
| ITF South Africa F2 | 2014/06/04 09:15 | Dean O'Brien v Brandon Laubser | 6-4,5-7,7-5 |