Di Matteo began his managerial career with Milton Keynes Dons, who he took to the League One playoffs in 2008–09 before leaving to return West Bromwich Albion to the Premier League. As caretaker manager of Chelsea, he steered the club to double title success, winning both the FA Cup and the club's first UEFA Champions League title in 2012, but was dismissed later that year. He then went on to coach Schalke 04 until May 2015 when he departed after seven months in charge, and had four months as manager of Aston Villa in 2016.