A quick right winger, Istead initially endeared himself to the terraces with his eagerness to run at defenders, and a headed goal in Pools`s League Cup victory at Sheffield Wednesday in 2003 helped his cause further. At the end of his second season at the club he was voted Young Player of the Season by the Pools supporters. Yet more than three years into his Pools career he remained a fringe player and as the 2004/05 ended he had made just one league start for the club despite more than 50 appearances from the substitutes` bench. Istead signed his first professional contract in the summer of 2005 and made infrequent appearances for the first team throughout the following season, scoring a late winner at Blackpool. He was released in May 2006, shortly after the club were relegated to League Two.