1999–2000 Port Vale F.C. season

The 1999–2000 season was Port Vale's 88th season of football in the English Football League, and sixth successive season in the First Division. Vale suffered relegation in 23rd place, some thirteen points adrift of safety. They also exited the FA Cup at the Third Round, and were knocked out of the League Cup at the First Round by fourth tier Chester City for the second consecutive season. The club spent nothing on transfers, but sold young players for some £1.5 million – despite this the club was heading towards bankruptcy. The club continued to gain one generation of players at the expense of the successful '90s generation; Martin Foyle, Paul Musselwhite and Ian Bogie departing, with fresh talent such as Micky Cummins and Mark Goodlad arriving in their place.

1999–2000 Port Vale F.C. season

The 1999–2000 season was Port Vale's 88th season of football in the English Football League, and sixth successive season in the First Division. Vale suffered relegation in 23rd place, some thirteen points adrift of safety. They also exited the FA Cup at the Third Round, and were knocked out of the League Cup at the First Round by fourth tier Chester City for the second consecutive season. The club spent nothing on transfers, but sold young players for some £1.5 million – despite this the club was heading towards bankruptcy. The club continued to gain one generation of players at the expense of the successful '90s generation; Martin Foyle, Paul Musselwhite and Ian Bogie departing, with fresh talent such as Micky Cummins and Mark Goodlad arriving in their place.