| Club: | Chelsea |
| Season: | 1955–56 |
| Manager: | Ted Drake |
| Chairman: | Joe Mears |
| Stadium: | Stamford Bridge |
| League: | First Division |
| League Result: | 16th |
| Cup1: | FA Cup |
| Cup1 Result: | Fifth round |
| Cup2: | FA Charity Shield |
| Cup2 Result: | Winners |
| Cup3: | European Cup |
| Cup3 Result: | DNP |
| League Topscorer: | Roy Bentley (14) |
| Season Topscorer: | Roy Bentley (16) |
| Largest Win: | 6–1 v Everton |
| Largest Loss: | 0–5 v Burnley |
| Highest Attendance: | |
| Lowest Attendance: | |
| Pattern B1: | _whitecollarplain |
| Pattern So1: | _whitetop |
| Leftarm1: | 0000ff |
| Body1: | 0000ff |
| Rightarm1: | 0000ff |
| Socks1: | 000000 |
| Pattern B2: | _whitecollarplain |
| Pattern So2: | _whitetop |
| Leftarm2: | ff0000 |
| Body2: | ff0000 |
| Rightarm2: | ff0000 |
| Socks2: | 000000 |
| Prevseason: | 1954–55 |
| Nextseason: | 1956–57 |
The 1955–56 season was Chelsea Football Club's forty-second competitive season. Chelsea began the season as defending league champions and won the FA Charity Shield, but thereafter performed poorly and ultimately finished 16th in the First Division. The club were also due to participate in the inaugural edition of the European Champions' Cup, but withdrew from the competition after pressure from the Football League.[1] [2]