The 49-year-old midlands-born midfielder began his career with Walsall in 1981, where he played upwards of 350 games – the highlight of which coming in the 1987/88 season when he helped guide the Saddlers to the third tier of English football via the play-offs.
In 1989 Shakespeare signed with then top-flight side Sheffield Wednesday for £300,000, featuring 17 times for the Hillsborough side before a 1990 switch to West Bromwich Albion.
After three years, a promotion and well over 100 games for the Baggies, Shakespeare took in spells at Grimsby Town, Scunthorpe United, Telford United and Hednesford Town before finally hanging up his boots in 2000 at the age of 36.
Shakespeare stayed in the game however, taking up a role as an Academy Coach with former side West Bromwich Albion, and later taking charge of the reserves.
In October 2006, Shakespeare took charge of the first team for a 2-0 win over Crystal Palace following the departure of Robson, but eventually left the west-midlands side to join Leicester City as Assistant Manager to Nigel Pearson in July 2008.
After following Pearson to Hull City in 2010, Shakespeare returned to take up his role as assistant once again in November 2011, and helping take The Foxes to the brink of promotion to the top-flight through the 2012/13 Championship Play-Offs.