Ground: Hardcourt outdoor
| ITF South Africa F2 | 2014/06/04 09:15 | Dean O'Brien v Brandon Laubser | 6-4,5-7,7-5 |
| ITF Mexico F3 | 2014/05/10 15:00 | Dean O'Brien v Kevin King | 3-6,2-6 |
| ITF Mexico F3 | 2014/05/09 15:00 | Dean O'Brien v Maximiliano Estevez | 4-6,6-0,6-1 |
| ITF Mexico F3 | 2014/05/06 15:00 | Manuel Sanchez v Dean O'Brien | 3-6,5-7 |
| ITF Mexico F2 | 2014/05/02 15:30 | Jorge Panta v Dean O'Brien | 6-2,6-2 |
| Challenger - San Luis Potosi | 2014/04/15 21:45 | Marcelo Arevalo v Dean O'Brien | 6-1,7-6 |
| Challenger San Luis Potosi Qual | 2014/04/13 18:25 | Dean O'Brien v Pavel Krainik | 6-4,6-4 |
| ITF Canada F2 | 2014/03/12 15:00 | Edward Corrie v Dean O'Brien | 5-7,6-4,6-3 |
| ITF South Africa F2 | 2014/06/05 08:00 | Nicolaas Scholtz v Ruan Roelofse | 3-6,6-3,7-6 |
| ITF South Africa F2 | 2014/06/04 09:30 | Nicolaas Scholtz v Augusto Laranja | 6-1,5-7,6-2 |
| ITF South Africa F2 | 2014/06/03 08:00 | Tyler Hochwalt v Nicolaas Scholtz | 6-4,6-7,4-6 |