A notable addition to the Pilgrims' squad was former England international Paul Gascoigne, who joined the club on a short-term basis, as a player-coach. Assigned his famous number 19 shirt for the forthcoming season, Gascoigne was presented in front of the media against his former club Newcastle, a game which he started. Gascoigne went on to make 10 appearances for Boston before leaving in October.
This season for Boston was also notable for their progression in the Carling Cup. Playing Champtionship side Luton Town was at first a daunting task for United, but they were in form following two consecutive league wins against Chester and Cambridge. The Pilgrims overcame Luton, winning 4–3, setting up a tie with Premier League club Fulham. 5373 people attended the second round tie at York Street, but Boston lost 4–1 at the hands of Chris Coleman's men. Playing for Fulham were many international players, such as Luis Boa Morte, Steed Malbranque, Brian McBride and Tomasz Radzinski.
It was a season of mixed results, with the team only winning 14 of a possible 46 league games. This saw Boston finish in a comfortable 16th position, but this was disappointing to the fans, considering what many had predicted in August.