 Stirling is a product of the Broadwater United football academy run by his father Clasford Stirling in Broadwater Farm, north London, he moved to join Luton Town as a junior and was added to the club's first team squad the 1999–2000 season.He did not make his debut until the following season when he was started against Swansea City in a league game on 16 September 2000.He would make a total of 10 appearances for Town in his first season, in all competitions.