 Ahead of the 2004–05 season, Guttridge was selected as club captain.Guttridge signed a three-year contract with Southend United in March 2005 for an undisclosed fee plus add-ons.After a slow start, he firmly established himself in the first-team and was given the opportunity to move into the role of a central midfielder from his usual wide midfielder role following a meeting with manager Steve Tilson.