The 1995–96 season was Port Vale's 84th season of football in the Football League, and second successive season in the First Division. Despite a poor start to the season, John Rudge led his side to a twelfth-place finish. The league highlights were two derby wins over Stoke City, had these results gone the other way then Stoke would have won automatic promotion to the Premier League. Vale's excellent mid-season form also raised hopes of a promotion campaign, but they faded away at the final stages. In the FA Cup, Vale achieved a celebrated upset by knocking out holders Everton with a 2–1 win at Vale Park. They were then eliminated at the Fifth Round, after taking Leeds United to a replay. They reached the final of the Anglo-Italian Cup, where they were defeated 5–2 by Genoa. These successes did not translate to the League Cup, where Vale exited at the First Round. Key new signings were Lee Mills and Player of the Year Jon McCarthy, though it was established star Tony Naylor who was the club's top-scorer.

The pre-season saw John Rudge make three key signings.. He bought Lee Mills from Derby County with Robin van der Laan going in the opposite direction with Vale receiving an additional £475,000; as well as Jon McCarthy from York City for a, still club record, £500,000; and defender Andy Hill from Manchester City for £200,000. He also signed Dutch defender Jermaine Holwyn from AFC Ajax for a £5,000 fee.

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