He later served as assistant manager for Everton, Watford, Aston Villa and the England national team.

[citation needed] Shakespeare rated his goal in a 2–2 League Cup draw against Chelsea in October 1984 as the best of his career.

[1] He played well over 350 games for the Saddlers, scoring 59 goals, and in 1989 he moved to Sheffield Wednesday, then in the First Division, for a fee of £300,000.

[citation needed] Shakespeare spent less than a year at Hillsborough, before moving to West Bromwich Albion for £275,000.

[citation needed] He scored twice from the penalty spot in Albion's first ever game in the Third Division, a 6–3 victory over Exeter City in August 1991.

In October 2006, following the departure of Bryan Robson and then his assistant Nigel Pearson (who had been caretaker manager for a period of four weeks), Shakespeare was given charge of the first team for one game pending the arrival of Tony Mowbray.

[3] Shakespeare left Albion in June 2008 to become Pearson's assistant manager at Leicester City,[4] a move that was confirmed on 1 July.

[22] He remained in this role until 19 July 2020, when Pearson and his backroom staff were sacked, despite there only being two games left in the season, and Watford being out of the relegation zone at that point.

[24] On 7 August 2020, Shakespeare was appointed assistant head coach to former Walsall teammate Dean Smith at Aston Villa,[25] the team he supported growing up.

[26] Shakespeare parted company with Aston Villa on 8 November 2021, the day after Smith had left the club.