 In June 2003, Stuart then joined fellow Third Division side Southend United for the upcoming 2003–04 season, saying he wanted to move nearer his family in London.He made his debut in the 3–0 home defeat against Mansfield Town in League Two on 23 August 2003.He was released from Southend United in May 2004 at the end of the season by manager Steve Tilson, having made 26 appearances in the Third Division for Southend United, collecting five yellow cards and failing to score.