O'Brien-Brady spent time in the youth systems at Fulham and Tottenham Hotspur before he joined the Academy at Huddersfield Town in the summer of 2020, where he was assigned an IDP (Individual Development Plan) to improve his dribbling and shooting on the move.[2] Primarily utilised as a winger, he was also played at left-back to help with his development.[3] He signed a one-year contract extension with the club option of a second year in June 2022.[4] On 15 January 2023, he joined Northern Premier League Premier Division side Hyde United on a one-month loan.[5]