Managed by José Mourinho, Chelsea marked their Centenary season by winning the Premier League title for the second consecutive year after defeating their closest challengers Manchester United 3–0 at Stamford Bridge on 29 April 2006.

Chelsea continued spending vast sums of money in their third season under the ownership of Roman Abramovich, signing Michael Essien from Lyon and Shaun Wright-Phillips from Manchester City for more than £20 million each.

In the Champions League, Chelsea aimed to improve upon their second straight semi-final placing the previous year, but exited the competition in the first knockout round to FC Barcelona.

In the FA Cup, they managed to improve on their third-round exit in the previous season, but fell short in the semi-final, losing 2–1 to Liverpool.

After winning the League Cup in the previous season, they failed to defend their title by taking an early third-round exit to Charlton Athletic on penalties.