 This proved to be a turning point and Guttridge was a major factor in helping Southend secure the 2005–06 League One title after a 1–0 home win over Bristol City on the final day of the season.Guttridge lost his place in the Southend first-team following their promotion and subsequently joined Leyton Orient on loan until 1 January 2007.He scored his first and what turned out to be only goal for the club in a 3–1 away win over Nottingham Forest on 16 December 2006.