He appeared in the famous Jimmy Glass game against Plymouth Argyle, in which the goalkeeper scored in the 94th minute to keep Carlisle United in the Football League.
[2] A ten-month spell at Darlington followed before Whitehead dropped down to the Football Conference in August 2003 for a season with Telford United.
Telford, and their chairman, were to go bankrupt at the end of the season, so Whitehead made the short move to newly promoted (to League Two) Shrewsbury Town.
He led the team out on 12 May hoping to lift the trophy but, unfortunately he will go down in history as the first captain to lose a competitive match at Wembley.
Whitehead left Kidderminster by mutual consent on 31 January 2008 and subsequently made his return to the New Bucks Head, signing an 18-month deal with Conference North side AFC Telford United.