Pearson originally began his career with football league side Oldham Athletic, where he made a handful of first team appearances. Having progressed through Oldham's youth system, he made several appearances for the reserve team before being promoted to the first team, making his first-team debut against Millwall in a 2-1 loss on 17 February 2007. In the summer of 2007, Pearson signed a one-year contract extension to remain at Boundary Park. Pearson was loaned out to Farsley Celtic of Conference National between October and December 2007.
Pearson joined Barrow in the summer of 2008; his highlight and lowlight at the club being in the 2008/09 FA Cup clash with then-Premier League side Middlesbrough. The game saw him receive an injury in the 52nd minute after a challenge with Marvin Emnes, where he sustained a double leg-break, which ruled him out for the remainder of the season.
Pearson made over 150 league appearances for Barrow, but he left the Cumbrian outfit when they were relegated in at the end of the 2012/13 season, which prompted his move to Airbus UK Broughton.
Following an outstanding couple of seasons at Airbus, Pearson was voted into the Welsh Premier League Team of the Season for two successive seasons before joining The Nomads in June 2016. Unfortunately, Pearson suffered a season of injury woe upon joining The Nomads, breaking his foot in one of his first training sessions with the Club, and then re-breaking it in another training session during his rehabilitation.
Pearson finally made his Nomads competitive debut in the 2017/18 UEFA Europa League First Qualifying Round victory over Finnish side, HJK Helsinki.