 He made his first-team debut for the Shrimpers on 22 October 2011 in a 4–1 win over Torquay United, replacing the injured Glenn Morris in the second half.Following an injury to first choice Southend United goalkeeper Paul Smith, Bentley was called upon to deputise and played in his first run of first-team matches in the 2012–13 season, making his full debut for Southend on 22 September 2012 against Exeter City, a match Southend won 2–1.Bentley went on to play further matches against Plymouth, and Burton Albion before Paul Smith returned to full fitness.