Donay O'Brien-Brady joined Posh following spells within the Tottenham Hotspur and Huddersfield Town Academy systems and made his first team debut for the club against the Terriers as a second half substitute on the opening day of the 2024-2025 season. 

O'Brien-Brady has been a regular within the club's Under 21 side during the 2023-2024 season as a number 10, but has been moved back into central midfield and thrived in that position. He is excellent on the ball, always looks for a progressive pass forward and has a solid temperament.