A year later he moved up the football pyramid again by signing for Boston United where he enjoyed two seasons, earning promotion to the Conference North.
In his final season as a player he spent a month back on loan with Boston United eleven years after last playing for the club.
At the end of the season Pearson and Boston earned promotion to the Conference North division after beating Bradford Park Avenue in the play-off final.
[7] During the course of the 2010–11 season United's management duo had departed to take over from Neil Woods at Grimsby Town[8] and speculation mounted that Pearson would be joining his former mentors at Blundell Park, Pearson was quick to quash the rumours saying that although he wanted to become a professional footballer he wanted to do it with Boston and was hopeful he could aid the club's promotion bid to the Conference Premier.
[9] The rumour had also unsettled Boston chairman David Newton who said his main aim was to keep Pearson at York Street following two outstanding seasons.
[14] Both moves caused issues between the two clubs and a court tribunal had to be set in November 2011 to settle the compensation Grimsby would have to pay Boston for both players.
[15] No sooner than a month into his career at Grimsby, he had fetched his first trophy for the club in helping Town lift the Lincolnshire Senior Cup after beating Lincoln City at Sincil Bank.
[20] Pearson continued his form and run in the team initially partnering Fleetwood Town loanee Nathan Pond for the first half of the 2012–13 season.
The club had already defended the Lincolnshire Senior Cup by yet again beating local rivals Lincoln City on a penalty shootout at Sincil Bank.
[24] Ahead of the 2013–14 season Pearson put pen to paper on a new one-year contract, with the player saying Blundell Park was the best place to be for his development.
[25] He played in the 2015 Conference Premier play-off final against Bristol Rovers at Wembley on 17 May 2015; following a 1–1 draw after extra time, Grimsby lost 5–3 in a penalty shoot-out.