He was loaned out to a number of lower division clubs, namely Clydebank, Alloa Athletic, Queen's Park and Hamilton Academical.
Stewart was first choice goalkeeper throughout the second half of season 2006–07 for First Division side Livingston, where he played the last dozen or so games after ousting Mariusz Liberda from the number one jersey.
After this he spent most of his début season in the stand, with manager Davie Irons preferring to list youth players Kieran Cannon and Ryan McWilliams as the back-up goalkeepers to Cuthbert.
[7] Stewart returned to Scotland during February 2013, playing three trial matches for Stranraer before signing for Cowdenbeath.
[8] On 27 August 2013, after the club's League Cup second round defeat at home to Livingston, Stewart had to be restrained by stewards as he argued with a fan as he headed up the tunnel at full-time.
[13] Stewart was appointed as co-manager of Junior club Kilwinning Rangers in February 2014 alongside former Queen of the South and Ayr United player Chris Strain.