O'Brien started his career at Aston Villa where he made the bench on several occasions as the youth side won the NextGen Series in 2013.
On 9 August 2016, he made his senior debut for Wigan in the EFL Cup as an 87th minute substitute in a 2–1 loss to Oldham Athletic.
[5] On 30 November 2018, O'Brien joined National League North side Alfreton Town on a deal until the end of the season.
[7] However, before making an appearance for Curzon, O'Brien joined Northern Premier League side Hyde United.
[8] On 11 October 2019, after six appearances with Hyde, O'Brien joined fellow Northern Premier League side Atherton Collieries.