The 2005–06 season was Chelsea F.C.'s 91st competitive season, 14th consecutive season in the Premier League and 100th year as a club. Managed by José Mourinho, Chelsea won the Premier League title for the second consecutive season. They also won the Community Shield.

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.

The team kit for the season was produced by Umbro and the shirt sponsor was Samsung Mobile, who replaced previous shirt sponsor Emirates Airlines. Chelsea's new home kit was all blue with gold accents. Their new away kit was light blue with black shorts and black accents. Their 3rd kit was similar to their away kit from the 2004–05 season, black with grey shorts and grey accents. The only difference was the addition of the new shirt sponsor and new club crest with modifications.

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