Challenger Columbus 2 Qual 11/19 16:20 45 Dean O'Brien v Hunter Tubert 2-6,7-6,2-6
Challenger Bogota Qual 11/06 15:00 46 Dean O'Brien v Marcelo Zormann 3-6,5-7
Challenger Bogota Qual 11/05 15:00 45 Dean O'Brien v Camilo Andres Erazo 3-6,6-2,6-3
Others 09/24 15:20 45 Dean O'Brien v Ante Pavic 2-6,3-6
Challenger Izmir Qual 09/17 09:00 45 Ruan Roelofse v Dean O'Brien 6-0,6-3
Challenger Aptos Qual 08/07 17:00 46 Cameron Norrie v Dean O'Brien 6-1,6-1
Challenger Aptos Qual 08/06 20:10 45 Michael Genender v Dean O'Brien 3-6,2-6
Challenger Dallas Qual 01/30 16:00 45 Dean O'Brien v Clay Thompson 4-6,2-6
Challenger Columbus 09/21 18:55 25 Dean O'Brien v Sekou Bangoura 3-6,1-6
Challenger Columbus Qual 09/20 16:10 44 Dean O'Brien v Herkko Pollanen 6-3,6-4
ITF Uzbekistan F4 06/10 06:25 - Temur Ismailov v Dean O'Brien 6-2,6-1
ITF Uzbekistan F4 06/09 07:40 - Dean O'Brien v Pavel Tsoy 6-3,6-4
Challenger Drummondville Qual 03/16 15:45 44 Adam El Mihdawy v Dean O'Brien 6-3,6-2
ITF Canada F2 Qual 03/08 18:00 - Dean O'Brien v Victor Krustev 2-6,7-6,4-6
ITF Canada F1 03/04 16:20 - Dean O'Brien v Filip Veger 2-6,2-6
ITF USA F28 10/15 18:30 - Adam El Mihdawy v Dean O'Brien 6-3,7-6
ITF Colombia F5 09/11 15:00 - Dean O'Brien v Fabiano De Paula 4-6,3-6
ITF Colombia F5 09/10 16:35 - Dean O'Brien v Pedro Bernardi 7-6,6-4
ITF Colombia F4 08/25 16:00 - Dean O'Brien v Fabiano De Paula 6-7,3-6
ITF France F11 06/18 08:00 - Nils Langer v Dean O'Brien 6-4,6-2
ITF South Africa F3 06/11 09:15 - Dean O'Brien v Ruan Roelofse 4-6,4-6
ITF South Africa F2 06/06 09:30 - Dean O'Brien v Nicolaas Scholtz 2-6,4-6
ITF South Africa F2 06/04 09:15 - Dean O'Brien v Brandon Laubser 6-4,5-7,7-5
ITF Mexico F3 05/10 15:00 - Dean O'Brien v Kevin King 3-6,2-6
ITF Mexico F3 05/09 15:00 - Dean O'Brien v Maximiliano Estevez 4-6,6-0,6-1
ITF Mexico F3 05/08 15:00 - Nicolas Meister v Dean O'Brien Retired
ITF Mexico F3 05/06 15:00 - Manuel Sanchez v Dean O'Brien 3-6,5-7
ITF Mexico F2 05/02 15:30 - Jorge Panta v Dean O'Brien 6-2,6-2
Challenger San Luis Potosi 04/15 21:45 25 Marcelo Arevalo v Dean O'Brien 6-1,7-6
Challenger San Luis Potosi Qual 04/13 18:25 44 Dean O'Brien v Pavel Krainik 6-4,6-4