Weston began his career in the youth academy of Manchester United, where he played for four years without making it into the first-team squad.

Weston moved to Ipswich Town in 1990, where he played for five years in the youth and reserve teams, including a 5-month loan stint with Stockport County.

[2] His identical twin brother Kenny was also on Ipswich's books without breaking through to the first team[3] and also moved on to coaching abroad, in his case in Australia.

He then moved on to work as the assistant coach at the University of Bridgeport in 2008 before setting up his own business, Weston Pro Soccer.

In March 2012 Weston was announced as technical director/head coach for USL Premier Development League club Ocala Stampede.