Michael Essien his contract on 12 March 2007. It was feared Essien would miss the 2008–09 Premier League season after sustaining anterior cruciate ligament damage on 5 September while playing for Ghana. However, on 7 March 2009, he came on as a substitute in the second half of the FA Cup match against Coventry City. In his second match back from the knee injury, Essien scored just before half-time to give Chelsea a vital away goal against Juventus in the Champions League first knockout round. Chelsea went on the draw the match 2–2 and through to the quarter-finals 3–2 on aggregate. He
Michael Essien a season-long loan deal with Real Madrid, reuniting him with his former manager at Chelsea, José Mourinho. At his introductory press conference with Real Madrid, Mourinho affectionally referred to Essien as "his son" while Essien referred to Mourinho as his "Daddy". On 3 November, Essien scored his first goal for Real Madrid. During the last match of the season – and Essien's last game as a Madrid player – Essien scored his second goal for Madrid, which he dedicated to Mourinho. Essien signed for Italian club Milan on a one-and-a-half-year contract on 27 January 2014. On 2 June 2015, Essien