Midfielder Istead began his career at Newcastle but left to join Hartlepool United in 2002 without making a single first team appearance. He played 64 times for Hartlepool and even became the youngest player ever to play for the club before his release in 2006.

Istead then went onto play for non league clubs Gateshead and Consett before rejoining his old Hartlepool boss Neale Cooper at Peterhead. After 22 appearances in Scotland he returned south of the border to join Ilkeston Town where David Holdsworth was then the manager.

Holdsworth swooped to resign the youngster for the Stags for the 2009 season using him 15 times at Field Mill. The midfielder was then sent to Conference North team Alfreton Town on a loan deal in December 2009 in pursuit of regular first team football.