After making his debut in a 1–1 draw with Huddersfield Town on the opening day of the 2008–09 season, Williams soon established himself as County's No.1, however in October 2008, he lost his first team place to on-loan keeper Fraser Forster. Forster was kept in goal for six games throughout October and into early November before his loan spell expired and Williams returned to his Number One slot. Until the middle of March, Williams was ever present for County, putting in match winning performances. On 30 March, Williams underwent an operation on his shoulder which kept him out for the remainder of the 2008–09 season. Despite making thirty-three appearance, Williams, nevertheless, was awarded Stockport County's Player of the Year. His performance saw also him being linked with a move to Premier League side Blackburn Rovers and Newcastle United and the club may sell him, as they faced financial problems.