 After being linked with a move to Leeds, Bentley proclaimed that he would not let the speculation of a potential move affect his performances.Over the summer of 2014 Bentley was linked with moves to Premier League clubs, but eventually remained at Southend, and in the early part of the following season he was considered for the England U21s, however he was not selected.In the 2014–15 season, Bentley broke Mervyn Cawston's club record of 10 consecutive home clean sheets with 12 in a row between October and April.