During the summer of 2009, Pressley was appointed as an assistant manager at Falkirk, following his retirement as a player. Following the resignation of manager Eddie May on 11 February 2010, Pressley was appointed Falkirk manager on a contract until the end of the 2009–10 season.[21] Falkirk were relegated to the First Division at the end of the 2009–10 season.[22] Despite failing to gain promotion back to the SPL at the first attempt, Falkirk extended his contract for another year.[22]
Pressley is 5/2 favourite with BetVictor to take the Swindon Town manager's job, following DiCanio's resignation from the English League 1 club.