The 2008-09 season was Chelsea Football Club's 94th competitive season, 17th consecutive season in the Premier League and 103rd year in existence as a football club.

After again finishing second to Manchester United in the Premier League the previous season, Chelsea sacked their manager Avram Grant, replacing him with the Brazilian Luiz Felipe Scolari, who had managed the Portugal national team at UEFA Euro 2008. The first few months of his management went according to plan, as Scolari's narrow 4–1–4–1 formation, using Ashley Cole and new arrival José Bosingwa as wing-backs, initially took the league by storm, leaving Chelsea top ahead of Liverpool after 13 games.

By the end of November, however, Scolari's Chelsea began to lose their form. They suffered a 3–1 defeat away to Roma in the Champions League and being eliminated from the League Cup at Stamford Bridge by Championship side Burnley on penalties. In the league, they had a 0–0 draw at home to Newcastle United, (who were later to be relegated). Chelsea lost a home league game for the first time since 2004 (and 86 matches) when they lost to Liverpool, and a second home league defeat to rivals Arsenal dropped Chelsea to second place.

Chelsea qualified for the knock-out stages of the Champions League with a 2–1 victory against Romanian champions CFR Cluj at Stamford Bridge in the final match of the group. During the winter months, they drew against West Ham United, Fulham, Hull City and League One's Southend United in the FA Cup. Chelsea suffered defeats away to Manchester United and Liverpool, which left them in fourth place during February which would mean a Champions League place would not be certain. Long-term injuries to Michael Essien and Joe Cole marked the period while Didier Drogba was not included frequently.

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