| Season | Competition |
Round Reached | Date |
Home | |
Away |
|
| 2007/2008 | Champions League | Final | Wed 21 May | Man. Utd. | v | Chelsea |
| played at Luzhniki Stadium, Moscow |
| F.A. Cup | 6th Round | Sat 08 Mar | Barnsley | 1 - 0 | Chelsea |
| League Cup | Final | Sun 24 Feb | Tottenham H. | 2 - 1 | Chelsea |
| after extra time, 90 minutes 1-1; played at Wembley |
| Charity Shield | Final | Sun 05 Aug | Chelsea | 1 - 1 | Man. Utd. |
| after extra time, 90 minutes 1-1, Manchester United won 3-0 on penalties; played at Wembley |
|
| 2006/2007 | Champions League | Semi Final | Tue 01 May | Liverpool | 1 - 0 | Chelsea |
| after extra time, 90 minutes 1-0, aggregate 1-1, Liverpool won 4-1 on penalties |
| F.A. Cup | Final | Sat 19 May | Chelsea | 1 - 0 | Man. Utd. |
| after extra time, 90 minutes 0-0; played at Wembley |
| League Cup | Final | Sun 25 Feb | Chelsea | 2 - 1 | Arsenal |
| played at Millennium Stadium, Cardiff |
| Charity Shield | Final | Sun 13 Aug | Chelsea | 1 - 2 | Liverpool |
| played at Millennium Stadium, Cardiff |
|
| 2005/2006 | Champions League | Last 16 Knockout Stage | Tue 07 Mar | Barcelona | 1 - 1 | Chelsea |
| Barcelona won 3-2 on aggregate |
| F.A. Cup | Semi Final | Sat 22 Apr | Chelsea | 1 - 2 | Liverpool |
| played at Old Trafford |
| League Cup | 3rd Round | Wed 26 Oct | Chelsea | 1 - 1 | Charlton Ath. |
| after extra time, 90 minutes 1-1, Charlton Athletic won 5-4 on penalties |
| Charity Shield | Final | Sun 07 Aug | Chelsea | 2 - 1 | Arsenal |
| played at Millennium Stadium, Cardiff |
|
| 2004/2005 | Champions League | Semi Final | Tue 03 May | Liverpool | 1 - 0 | Chelsea |
| F.A. Cup | 5th Round | Sun 20 Feb | Newcastle Utd. | 1 - 0 | Chelsea |
| League Cup | Final | Sun 27 Feb | Chelsea | 3 - 2 | Liverpool |
| after extra time, 90 minutes 1-1 |
|
| 2003/2004 | Champions League | Semi Final | Wed 05 May | Chelsea | 2 - 2 | Monaco |
| Monaco won 5-3 on aggregate |
| F.A. Cup | 5th Round | Sun 15 Feb | Arsenal | 2 - 1 | Chelsea |
| League Cup | Quarter Final | Wed 17 Dec | Aston Villa | 2 - 1 | Chelsea |
|
| 2002/2003 | UEFA Cup | 1st Round | Thu 03 Oct | Viking | 4 - 2 | Chelsea |
| Viking won 5-4 on aggregate |
| F.A. Cup | 6th Round Replay | Tue 25 Mar | Chelsea | 1 - 3 | Arsenal |
| League Cup | 5th Round | Tue 17 Dec | Man. Utd. | 1 - 0 | Chelsea |
|
| 2001/2002 | F.A. Cup | Final | Sat 04 May | Chelsea | 0 - 2 | Arsenal |
| played at Millennium Stadium, Cardiff |
| League Cup | Semi Final | Wed 23 Jan | Tottenham H. | 5 - 1 | Chelsea |
|
| 2000/2001 | F.A. Cup | 5th Round | Sun 18 Feb | Arsenal | 3 - 1 | Chelsea |
| League Cup | 3rd Round | Wed 01 Nov | Liverpool | 2 - 1 | Chelsea |
| after extra time, 90 minutes 1-1 |
|
| 1999/2000 | F.A. Cup | Final | Sat 20 May | Chelsea | 1 - 0 | Aston Villa |
| played at Wembley |
| League Cup | 3rd Round | Wed 13 Oct | Chelsea | 0 - 1 | Huddersfield |
|
| 1998/1999 | F.A. Cup | 6th Round Replay | Wed 10 Mar | Chelsea | 0 - 2 | Man. Utd. |
| League Cup | Quarter Final | Tue 01 Dec | Wimbledon | 2 - 1 | Chelsea |
|
| 1997/1998 | F.A. Cup | 3rd Round | Sun 04 Jan | Chelsea | 3 - 5 | Man. Utd. |
| League Cup | Final | Sun 29 Mar | Chelsea | 2 - 0 | Middlesbrough |
| after extra time, 90 minutes 0-0; played at Wembley |
|
| 1996/1997 | F.A. Cup | Final | Sat 17 May | Chelsea | 2 - 0 | Middlesbrough |
| played at Wembley |
| League Cup | 3rd Round | Tue 22 Oct | Bolton Wdrs. | 2 - 1 | Chelsea |
|
| 1995/1996 | F.A. Cup | Semi Final | Sun 31 Mar | Man. Utd. | 2 - 1 | Chelsea |
| played at Villa Park |
| League Cup | 2nd Round | Wed 04 Oct | Chelsea | 0 - 1 | Stoke City |
| Stoke City won 1-0 on aggregate |
|
| 1994/1995 | F.A. Cup | 4th Round Replay | Wed 08 Feb | Chelsea | 1 - 1 | Millwall |
| after extra time, 90 minutes 1-1, Millwall won 5-4 on penalties |
| League Cup | 3rd Round | Wed 26 Oct | West Ham Utd. | 1 - 0 | Chelsea |
|
| 1993/1994 | F.A. Cup | Final | Sat 14 May | Man. Utd. | 4 - 0 | Chelsea |
| played at Wembley |
| League Cup | 3rd Round | Tue 26 Oct | Man. City | 1 - 0 | Chelsea |
|
| 1992/1993 | F.A. Cup | 3rd Round | Wed 13 Jan | Middlesbrough | 2 - 1 | Chelsea |
| League Cup | Quarter Final | Wed 06 Jan | Crystal Palace | 3 - 1 | Chelsea |
|
| 1991/1992 | F.A. Cup | 6th Round Replay | Wed 18 Mar | Sunderland | 2 - 1 | Chelsea |
| League Cup | 2nd Round | Tue 08 Oct | Tranmere Rvs. | 3 - 1 | Chelsea |
| Tranmere Rovers won 4-2 on aggregate |
| (Full Members) | Southern Section Final | Wed 29 Jan | Chelsea | 1 - 3 | Southampton |
| Southampton won 5-1 on aggregate |
|
| 1990/1991 | F.A. Cup | 3rd Round | Sat 05 Jan | Chelsea | 1 - 3 | Oxford Utd. |
| League Cup | Semi Final | Wed 27 Feb | Sheff. Wed. | 3 - 1 | Chelsea |
| Sheffield Wednesday won 5-1 on aggregate |
| (Full Members) | Southern Section Quarter-Final | Mon 18 Feb | Chelsea | 1 - 1 | Luton Town |
| after extra time, 90 minutes 1-1, Luton Town won 4-1 on penalties |
|
| 1989/1990 | F.A. Cup | 4th Round | Sat 27 Jan | Bristol City | 3 - 1 | Chelsea |
| League Cup | 2nd Round | Wed 04 Oct | Scarborough | 3 - 2 | Chelsea |
| Scarborough won 4-3 on aggregate |
| (Full Members) | Final | Sun 25 Mar | Chelsea | 1 - 0 | Middlesbrough |
| at Wembley |
|
| 1988/1989 | F.A. Cup | 3rd Round | Sat 07 Jan | Barnsley | 4 - 0 | Chelsea |
| League Cup | 2nd Round | Wed 12 Oct | Chelsea | 2 - 2 | Scunthorpe U. |
| Scunthorpe United won 6-3 on aggregate |
|
| 1987/1988 | F.A. Cup | 4th Round | Sat 30 Jan | Man. Utd. | 2 - 0 | Chelsea |
| League Cup | 2nd Round | Wed 07 Oct | Chelsea | 3 - 2 | Reading |
| Reading won 5-4 on aggregate |
|
| 1986/1987 | F.A. Cup | 4th Round | Sun 01 Feb | Watford | 1 - 0 | Chelsea |
| League Cup | 3rd Round | Tue 28 Oct | Cardiff City | 2 - 1 | Chelsea |
|
| 1985/1986 | F.A. Cup | 4th Round | Sun 26 Jan | Chelsea | 1 - 2 | Liverpool |
| League Cup | Quarter Final Replay | Wed 29 Jan | Chelsea | 0 - 2 | Q.P.R. |
|
| 1984/1985 | F.A. Cup | 4th Round | Mon 04 Feb | Chelsea | 2 - 3 | Millwall |
| League Cup | Semi Final | Mon 04 Mar | Chelsea | 2 - 3 | Sunderland |
| Sunderland won 5-2 on aggregate |
|
| 1983/1984 | F.A. Cup | 3rd Round | Sat 07 Jan | Blackburn R. | 1 - 0 | Chelsea |
| League Cup | 3rd Round | Wed 09 Nov | Chelsea | 0 - 1 | West Brom. |
|
| 1982/1983 | F.A. Cup | 4th Round | Sat 29 Jan | Derby County | 2 - 1 | Chelsea |
| League Cup | 3rd Round | Tue 09 Nov | Notts. County | 2 - 0 | Chelsea |
|
| 1981/1982 | F.A. Cup | 6th Round | Sat 06 Mar | Chelsea | 2 - 3 | Tottenham H. |
| League Cup | 3rd Round | Wed 11 Nov | Wigan Ath. | 4 - 2 | Chelsea |
|
| 1980/1981 | F.A. Cup | 3rd Round | Sat 03 Jan | Southampton | 3 - 1 | Chelsea |
| League Cup | 2nd Round | Wed 03 Sep | Chelsea | 1 - 1 | Cardiff City |
| Cardiff City won 2-1 on aggregate |
|
| 1979/1980 | F.A. Cup | 3rd Round | Mon 14 Jan | Chelsea | 0 - 1 | Wigan Ath. |
| League Cup | 2nd Round | Tue 04 Sep | Chelsea | 1 - 2 | Plymouth Arg. |
| Plymouth Argyle won 4-3 on aggregate |
|
| 1978/1979 | F.A. Cup | 3rd Round | Mon 15 Jan | Man. Utd. | 3 - 0 | Chelsea |
| League Cup | 2nd Round | Tue 29 Aug | Bolton Wdrs. | 2 - 1 | Chelsea |
|
| 1977/1978 | F.A. Cup | 5th Round Replay | Mon 27 Feb | Chelsea | 1 - 2 | Orient |
| League Cup | 2nd Round | Tue 30 Aug | Liverpool | 2 - 0 | Chelsea |
|
| 1976/1977 | F.A. Cup | 3rd Round Replay | Wed 12 Jan | Chelsea | 0 - 3 | Southampton |
| after extra time, 90 minutes 0-0 |
| League Cup | 4th Round | Tue 26 Oct | Arsenal | 2 - 1 | Chelsea |
|
| 1975/1976 | F.A. Cup | 5th Round | Sat 14 Feb | Chelsea | 2 - 3 | Crystal Palace |
| League Cup | 2nd Round | Wed 10 Sep | Crewe Alex. | 1 - 0 | Chelsea |
|
| 1974/1975 | F.A. Cup | 4th Round | Sat 25 Jan | Chelsea | 0 - 1 | Birmingham C. |
| League Cup | 3rd Round 2nd Replay | Tue 22 Oct | Stoke City | 6 - 2 | Chelsea |
|
| 1973/1974 | F.A. Cup | 3rd Round Replay | Tue 15 Jan | Q.P.R. | 1 - 0 | Chelsea |
| League Cup | 2nd Round | Mon 08 Oct | Stoke City | 1 - 0 | Chelsea |
|
| 1972/1973 | F.A. Cup | 6th Round Replay | Tue 20 Mar | Arsenal | 2 - 1 | Chelsea |
| League Cup | Semi Final | Wed 03 Jan | Norwich City | 1 - 0 | Chelsea |
| Norwich City won 3-2 on aggregate |
|
| 1971/1972 | F.A. Cup | 5th Round | Sat 26 Feb | Orient | 3 - 2 | Chelsea |
| League Cup | Final | Sat 04 Mar | Stoke City | 2 - 1 | Chelsea |
| played at Wembley |
|
| 1970/1971 | F.A. Cup | 4th Round | Sat 23 Jan | Chelsea | 0 - 3 | Man. City |
| League Cup | 4th Round | Wed 28 Oct | Man. Utd. | 2 - 1 | Chelsea |
|
| 1969/1970 | F.A. Cup | Final Replay | Wed 29 Apr | Chelsea | 2 - 1 | Leeds Utd. |
| after extra time, 90 minutes 1-1; played at Old Trafford |
| League Cup | 4th Round | Wed 15 Oct | Carlisle Utd. | 1 - 0 | Chelsea |
|
| 1968/1969 | F.A. Cup | 6th Round | Sat 01 Mar | Chelsea | 1 - 2 | West Brom. |
| League Cup | 3rd Round Replay | Wed 02 Oct | Derby County | 3 - 1 | Chelsea |
|
| 1967/1968 | F.A. Cup | 6th Round | Sat 30 Mar | Birmingham C. | 1 - 0 | Chelsea |
| League Cup | 2nd Round | Wed 13 Sep | Middlesbrough | 2 - 1 | Chelsea |
|
| 1966/1967 | F.A. Cup | Final | Sat 20 May | Tottenham H. | 2 - 1 | Chelsea |
| played at Wembley |
| League Cup | 3rd Round Replay | Mon 17 Oct | Chelsea | 1 - 3 | Blackpool |
|
| 1965/1966 | F.A. Cup | Semi Final | Sat 23 Apr | Sheff. Wed. | 2 - 0 | Chelsea |
| played at Villa Park |
|
| 1964/1965 | F.A. Cup | Semi Final | Sat 27 Mar | Liverpool | 2 - 0 | Chelsea |
| played at Villa Park |
| League Cup | Final | Mon 05 Apr | Leicester City | 0 - 0 | Chelsea |
| Chelsea won 3-2 on aggregate |
|
| 1963/1964 | F.A. Cup | 4th Round | Sat 25 Jan | Chelsea | 1 - 2 | Huddersfield |
| League Cup | 2nd Round | Wed 25 Sep | Swindon Town | 3 - 0 | Chelsea |
|
| 1962/1963 | F.A. Cup | 5th Round | Sat 16 Mar | Man. Utd. | 2 - 1 | Chelsea |
|
| 1961/1962 | F.A. Cup | 3rd Round | Sat 06 Jan | Liverpool | 4 - 3 | Chelsea |
|
| 1960/1961 | F.A. Cup | 3rd Round | Sat 07 Jan | Chelsea | 1 - 2 | Crewe Alex. |
| League Cup | 4th Round | Wed 14 Dec | Portsmouth | 1 - 0 | Chelsea |
|
| 1959/1960 | F.A. Cup | 4th Round | Sat 30 Jan | Chelsea | 1 - 2 | Aston Villa |
|
| 1958/1959 | F.A. Cup | 4th Round | Sat 24 Jan | Chelsea | 1 - 2 | Aston Villa |
|
| 1957/1958 | F.A. Cup | 4th Round Replay | Wed 29 Jan | Darlington | 4 - 1 | Chelsea |
| after extra time, 90 minutes ?-? |
|
| 1956/1957 | F.A. Cup | 4th Round | Sat 26 Jan | Tottenham H. | 4 - 0 | Chelsea |
|
| 1955/1956 | F.A. Cup | 5th Round | Sat 18 Feb | Everton | 1 - 0 | Chelsea |
|
| 1954/1955 | F.A. Cup | 5th Round | Sat 19 Feb | Notts. County | 1 - 0 | Chelsea |
|
| 1953/1954 | F.A. Cup | 3rd Round | Sat 09 Jan | West Brom. | 1 - 0 | Chelsea |
|
| 1952/1953 | F.A. Cup | 5th Round | Sat 14 Feb | Chelsea | 0 - 4 | Birmingham C. |
|
| 1951/1952 | F.A. Cup | Semi Final Replay | Mon 07 Apr | Arsenal | 3 - 0 | Chelsea |
| played at White Hart Lane |
|
| 1950/1951 | F.A. Cup | 5th Round Replay | Wed 14 Feb | Fulham | 3 - 0 | Chelsea |
|
| 1949/1950 | F.A. Cup | Semi Final Replay | Sat 25 Mar | Chelsea | 0 - 1 | Arsenal |
| after extra time, 90 minutes 0-0; played at White Hart Lane |
|
| 1948/1949 | F.A. Cup | 5th Round | Sat 12 Feb | West Brom. | 3 - 0 | Chelsea |
|
| 1947/1948 | F.A. Cup | 4th Round | Sat 24 Jan | Man. City | 2 - 0 | Chelsea |
| after extra time, 90 minutes 0-0 |
|
| 1946/1947 | F.A. Cup | 4th Round Replay | Wed 29 Jan | Derby County | 1 - 0 | Chelsea |
| after extra time, 90 minutes 0-0 |
|
| 1945/1946 | F.A. Cup | 5th Round | Tue 12 Feb | Aston Villa | 1 - 0 | Chelsea |
| Aston Villa won 2-0 on aggregate |
|
| 1938/1939 | F.A. Cup | 6th Round | Sat 04 Mar | Chelsea | 0 - 1 | Grimsby Town |
|
| 1937/1938 | F.A. Cup | 3rd Round | Sat 08 Jan | Chelsea | 0 - 1 | Everton |
|
| 1936/1937 | F.A. Cup | 4th Round | Sat 30 Jan | Millwall | 3 - 0 | Chelsea |
|
| 1935/1936 | F.A. Cup | 5th Round Replay | Mon 24 Feb | Fulham | 3 - 2 | Chelsea |
|
| 1934/1935 | F.A. Cup | 3rd Round Replay | Wed 16 Jan | Luton Town | 2 - 0 | Chelsea |
|
| 1933/1934 | F.A. Cup | 5th Round | Sat 17 Feb | Stoke City | 3 - 1 | Chelsea |
|
| 1932/1933 | F.A. Cup | 3rd Round | Sat 14 Jan | Brighton & HA | 2 - 1 | Chelsea |
|
| 1931/1932 | F.A. Cup | Semi Final | Sat 12 Mar | Chelsea | 1 - 2 | Newcastle Utd. |
| played at Huddersfield |
|
| 1930/1931 | F.A. Cup | 6th Round Replay | Wed 04 Mar | Chelsea | 0 - 3 | Birmingham |
|
| 1929/1930 | F.A. Cup | 3rd Round | Sat 11 Jan | Arsenal | 2 - 0 | Chelsea |
|
| 1928/1929 | F.A. Cup | 5th Round Replay | Wed 20 Feb | Portsmouth | 1 - 0 | Chelsea |
|
| 1927/1928 | F.A. Cup | 3rd Round | Sat 14 Jan | Wolves | 2 - 1 | Chelsea |
|
| 1926/1927 | F.A. Cup | 6th Round Replay | Wed 09 Mar | Cardiff City | 3 - 2 | Chelsea |
|
| 1925/1926 | F.A. Cup | 4th Round | Sat 30 Jan | Crystal Palace | 2 - 1 | Chelsea |
|
| 1924/1925 | F.A. Cup | 1st Round | Sat 10 Jan | Birmingham | 2 - 0 | Chelsea |
|
| 1923/1924 | F.A. Cup | 1st Round Replay | Wed 16 Jan | Southampton | 2 - 0 | Chelsea |
|
| 1922/1923 | F.A. Cup | 2nd Round Replay | Wed 07 Feb | Southampton | 1 - 0 | Chelsea |
|
| 1921/1922 | F.A. Cup | 1st Round | Sat 07 Jan | Chelsea | 2 - 4 | West Brom. |
|
| 1920/1921 | F.A. Cup | 4th Round | Sat 05 Mar | Cardiff City | 1 - 0 | Chelsea |
|
| 1919/1920 | F.A. Cup | Semi Final | Sat 27 Mar | Aston Villa | 3 - 1 | Chelsea |
| played at Bramall Lane |
|
| 1914/1915 | F.A. Cup | Final | Sat 24 Apr | Sheff. Utd. | 3 - 0 | Chelsea |
| played at Old Trafford |
|
| 1913/1914 | F.A. Cup | 1st Round Replay | Wed 14 Jan | Chelsea | 0 - 1 | Millwall |
|
| 1912/1913 | F.A. Cup | 2nd Round Replay | Wed 05 Feb | The Wednesday | 6 - 0 | Chelsea |
|
| 1911/1912 | F.A. Cup | 2nd Round | Sat 03 Feb | Bradford City | 2 - 0 | Chelsea |
|
| 1910/1911 | F.A. Cup | Semi Final | Sat 25 Mar | Newcastle Utd. | 3 - 0 | Chelsea |
| played at Birmingham City |
|
| 1909/1910 | F.A. Cup | 2nd Round | Sat 05 Feb | Chelsea | 0 - 1 | Tottenham H. |
|
| 1908/1909 | F.A. Cup | 2nd Round | Sat 06 Feb | Blackburn R. | 2 - 1 | Chelsea |
|
| 1907/1908 | F.A. Cup | 2nd Round | Sat 01 Feb | Man. Utd. | 1 - 0 | Chelsea |
|
| 1906/1907 | F.A. Cup | 1st Round Replay | Wed 16 Jan | Chelsea | 0 - 1 | Lincoln City |
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