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The 2005–06 season was Chelsea F.C.'s 92nd 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 season was momentous for Chelsea's incredible start to the season where they recorded the most dominant first half of a Premier League season in history. They won a record 9 games in a row at the start of the season, which culminated in another record holding 17 wins out of the first 19 games. As of 2017 Chelsea 2005-06 hold joint records for most wins at home in a season (18) and fewest home defeats in a season (0).