A left-sided attacking midfielder who turned professional at Walsall in 1981 before eventually moving on to Sheffield Wednesday in 1989. Playing alongside captain Nigel Pearson, he made just 17 appearances for the Owls - his only spell in the top flight.
Within a year he dropped down to join West Brom and then Grimsby Town.
There were short spells at Scunthorpe, Telford and Hednesford before retirement, but he had already returned to work for former club West Brom as Football in the Community Officer in 1999.
Under Manager Gary Megson, Shakespeare became Youth Team Coach and then Reserve Team Coach, and also worked for next Manager Bryan Robson.
Following Robson's departure, Nigel Pearson became Caretaker Manager for four games, but with the imminent arrival of Tony Mowbray, Pearson stepped down and Shakespeare took charge for the 2-0 win at Crystal Palace in the interim.
Shakespeare remained on Mowbray's coaching staff, but after the Baggies won the Championship in 2008 he left to become Pearson's Assistant and First Team Coach at Leicester City.
He came with Pearson to Hull City in the same capacity in June 2010.