friendly home win against Rotherham United, although he was unsuccessful in his attempt to earn a professional contract with the club. In August 2006, Wilson signed a one-year deal with Colchester United. Similarly to his time at Charlton, Wilson played regularly for the club's reserve team throughout the 2006–07 season, but did not make any first-team appearances. He was loaned out to Conference South club Welling United in December 2006. He made his debut for Welling in the club's 1–0 win away at Cambridge City, but was sent-off after just 27 minutes for violent conduct. He returned to first-team action in Welling's 0–0 draw with Basingstoke Town at Park View Road in the FA Trophy, and went on to play four times for Welling during his one-month loan spell at the club. On returning to Layer Road, Wilson was released at the end of the 2006–07 season, without making a first-team appearance for Colchester. Ahead of the 2007–08 season, Wilson spent pre-season trialling at Brentford and Stockport County respectively, training with Stockport for a number of weeks and playing in several pre-season friendlies, but was ultimately not offered a contract. Stevenage Wilson signed for Stevenage of the Conference Premier on 16 August 2007, joining on a one-year contract. Manager Mark Stimson gave Wilson his Stevenage debut a day after signing for the club, coming on as an 86th-minute substitute in Stevenage's 3–0 win against Weymouth on 17 August 2007. Wilson played 27 times during his first season at Stevenage, with the majority of his appearances coming in the second half of 2007–08 season. The following season under the new management of Graham Westley, Wilson played regularly in both the full-back position and at right midfield. Wilson scored his first professional goal in Stevenage's 3–1 away win at Barrow on 30 August 2008, taking advantage of a goalkeeping error in the 75th minute of the match to secure Stevenage's first win of the 2008–09 season. He was also sent-off for the first time in Stevenage colours in the club's 3–1 home defeat to Histon in November 2008, picking up the red card for "offensive language". Wilson returned to the first-team at the start of December and remained in the first-team until the end of the season. He subsequently played in both of Stevenage's Conference Premier play-off games against Cambridge United, as the club lost 4–3 on aggregate. Wilson's versatility also came