The 2008–09 season was Port Vale's 97th season of football in the Football League, and first season in League Two, following their relegation from League One. After a poor start to the season manager Lee Sinnott was sacked in September, and was replaced by Dean Glover. Despite a brief period of improvement, Vale then slipped back down the table to finish in eighteenth place. The team were also poor in the cup competitions, exiting the FA Cup at the Second Round, and both the League Cup and the League Trophy at the First Round. Marc Richards was the club's top scorer with eleven goals, and goalkeeper Joe Anyon was Player of the Year despite breaking his leg towards the end of the season.

The pre-season saw manager Lee Sinnott sign non-league midfielder Rob Taylor, former Hereford United defender John McCombe, and former Middlesbrough midfielder Steve Thompson. Both players cited Sinnott as their reason for joining the club. He also added experienced defender (Wycombe Wanderers); midfielder Anthony Griffith (Doncaster Rovers); and attacking midfielder Louis Dodds (Leicester City) to the squad.Lee Collins also joined on an extended loan from Wolverhampton Wanderers, and would sign a permanent contract with the club in January. Stockley was appointed captain, and most of these players would become key for the club over the next few seasons. Just before the season's start, teenage Tom Taiwo also arrived on a month loan from Chelsea, as did Plymouth Argyle youngster Damien McCrory. The club was aiming for an immediate return to League One, and fans got behind the club with record high season ticket sales of over 6,000.

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