 He finally made his Manchester United debut on 28 October, starting the 2–0 League Cup win at home to Bury, and played once more that season, again in the League Cup.Having failed to establish himself at Old Trafford, despite appearing in both the Champions League and the Premier League, Wilson left to join Middlesbrough in August 2001 for £1.5 million, as part of a £3.5 million deal that also took his teammate Jonathan Greening to the Riverside.Unable to settle at Boro, but scoring twice in the League Cup against Northampton and Brentford, he had loan spells with Stoke City, Swansea City, Sheffield Wednesday, Doncaster Rovers, and finally Livingston.