Prior to the 1999–2000 season, Stimson spent a short period on trial at another of his former clubs, Gillingham, but manager Peter Taylor decided against offering him a contract and he instead joined Isthmian League club Canvey Island. He helped the "Gulls" win the FA Trophy in the 2000–01 season, setting up the only goal and winning the man of the match award in Canvey's 1–0 defeat of Forest Green Rovers in the final. He was also selected to play for the England National Game XI, the national team for semi-professional players, earning one cap against an equivalent team from the United States. He left Canvey in May 2002 to join Grays Athletic as player-coach.