Sheffield born Pearson, aged 25, started his footballing career at Rotherham United where he was released during the summer of 2009.
In 2012, Pearson joined Leicester City, then competing in the Football League Championship who were then managed by his father Nigel Pearson.
Loan spells at Carlisle United, Wrexham and Peterborough United would follow before joining North-West London club Barnet on non-contract terms in 2016.
Following a knee injury, he would join up with The Sky Blues of Coventry City Football Club in August 2017 yet would leave later that month having made no appearances for the West Midlands club.
James would then sign for Worcestershire club Kidderminster Harriers, competing in the National League North, scoring once in the process.
In July 2018, Pearson signed a one year deal with Macclesfield Town Football Club.