He was at the Football Club for eight seasons as assistant manager, caretaker manager and permanent manager and played a vital role in a journey which saw City rise from League 1 to Premier League winners and to UEFA Champions League Quarter-Finalists.
Between 1981 and 1998, as a midfielder, Shakespeare made over 350 appearances for Walsall and played in the old First Division with Sheffield Wednesday, where he was a team mate of Nigel Pearson. He also starred in over 100 games for both West Bromwich Albion and Grimsby Town, before having a brief spell at Scunthorpe United.
In 1999, he returned West Brom as a 'Football in the Community Officer' before coaching at the academy and then, in 2006, overseeing the reserve team. When manager Bryan Robson left The Hawthorns in October 2006, his assistant, Pearson, was caretaker manager for four weeks. When he departed, meanwhile, Craig was put in charge for one game, a 2-0 victory over Crystal Palace, before Tony Mowbray was appointed as the permanent manager.
In June 2008, Craig and Steve Walsh arrived at Leicester City, newly relegated to League 1, as part of Pearson's coaching team. They won the League 1 title in 2009 and reached the Championship Play-Offs in 2010. The trio then returned to Leicester in October 2011 after a 17-month spell at Hull City and won the Championship title in 2014 before also masterminding the 'Great Escape' from relegation in 2015.
When Pearson left King Power Stadium in the summer of 2015, though, Shakespeare and Walsh continued as assistant managers under Claudio Ranieri, famously winning the Premier League title during the 2015/16 season.
In February 2017, with the Club in the bottom three of the Premier League, Ranieri left and Shakespeare became caretaker manager in challenging circumstances.
However, he became the first English manager to win his first five Premier League games. These were in a run of six consecutive victories which also included a win over FC Sevilla in the Champions League, a result which saw Leicester City qualify for the quarter-finals. They finished the season in 12th place. In the summer, Shakespeare was rewarded with a three-year contract. He also took on a coaching role with England which lasted until manager Sam Allardyce lost his job soon afterwards.
The new season opened with difficult early fixtures against Arsenal, Manchester United, Chelsea and Liverpool and, after gaining only one win and six points from his first eight games, Shakespeare departed in October 2017.
His assistant, Michael Appleton, took temporary charge until Claude Puel was appointed. Craig was well respected by the Blue Army fans who appreciated his dedication to the Club and his contribution to the most successful period in Leicester's history.
Three months after leaving King Power Stadium, Craig was appointed first team coach at Everton, rejoining Walsh and working under manager Allardyce. He left Goodison Park when Allardyce was dismissed in May 2018 before linking up with Pearson once more as assistant manager at Watford in December 2019, a role he left in July 2020. After spells Dean Smith's assistant at Aston Villa and Norwich City, Shakespeare returned to Leicester as a First Team Coach - again with Smith in charge - for the end of the 2022/23 season.