Ground: Hardcourt outdoor
| 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 Canada F1 | 2014/03/06 15:00 | Richard Gabb v Dean O'Brien | 5-7,6-4,6-3 |
| ITF Canada F1 | 2014/03/05 18:10 | Adam El Mihdawy v Dean O'Brien | 4-6,4-6 |