| ITF M15 Brisbane Qual | 08/10 01:30 | - | Pratik Navin v James O'Brien | View | |
| UTR Pro Lovedale | 08/03 05:10 | 28 | James O'Brien v Cooper Errey | CANC | |
| UTR Pro Lovedale | 08/01 00:40 | - | Elijah Cham v James O'Brien | 5-7,6-4,6-2 | |
| UTR Pro Lovedale | 07/30 01:00 | - | Nathan Boniel v James O'Brien | Walkover | |
| UTR Pro Lovedale | 07/29 02:50 | - | Luka Vujacic v James O'Brien | 1-6,7-6,6-7 | |
| UTR Pro Lovedale | 07/28 00:00 | - | Jera Staley v James O'Brien | 6-2,6-4 | |
| UTR Pro Lovedale | 06/03 01:30 | - | Eric Tripathi v James O'Brien | Retired | |
| UTR Pro Lovedale | 06/03 00:00 | - | Scott Jones v James O'Brien | CANC | |
| UTR Pro Lovedale | 06/01 00:00 | 29 | James O'Brien v SS Racing Roma U19 | 2-6,1-6 | |
| UTR Pro Lovedale | 05/30 23:00 | 28 | James O'Brien v Jesse Gothelf | 6-1,6-4 | |
| UTR Pro Lovedale | 05/30 00:50 | - | James O'Brien v Scott Jones | 4-6,3-6 | |
| UTR Pro Lovedale | 05/29 00:20 | - | James O'Brien v Jera Staley | 6-3,6-4 |