Head to Head Summary for Chelsea v Middlesbrough.
League Matches versus Middlesbrough
| Played | Won | Drawn | Lost | For | Against | TTL Att | AVG Att | |
| Home | 53 | 35 | 13 | 5 | 102 | 37 | 1,710,594 | 32,275 |
| Away | 53 | 14 | 16 | 23 | 61 | 81 | 1,216,717 | 22,957 |
| Total | 106 | 49 | 29 | 28 | 163 | 118 | 2,927,311 | 27,616 |
| Games since last league defeat: | Home: 19 | Away: 3 | All: 7 |
| Games since last league draw: | Home: 6 | Away: 7 | All: 12 |
| Games since last league win: | Home: 0 | Away: 0 | All: 0 |
| 357 Chelsea players have made League Appearances against Middlesbrough
| 94 Chelsea players have scored League Goals against Middlesbrough
|
F.A.Cup Matches versus Middlesbrough
| Played | Won | Drawn | Lost | For | Against | TTL Att | AVG Att | |
| Home | 1 | 1 | 0 | 0 | 1 | 0 | 29,796 | 29,796 |
| Away / Neutral | 4 | 3 | 0 | 1 | 7 | 2 | 155,214 | 38,804 |
| Total | 5 | 4 | 0 | 1 | 8 | 2 | 185,010 | 37,002 |
| Games since last F.A. Cup defeat: | Home: 1 | Away: 3 | All: 4 |
| Games since last F.A. Cup draw: | Home: 1 | Away: 4 | All: 5 |
| Games since last F.A. Cup win: | Home: 0 | Away: 0 | All: 0 |
| 64 Chelsea players have made FA Cup Appearances against Middlesbrough
| 7 Chelsea players have scored FA Cup Goals against Middlesbrough
|
League Cup Matches versus Middlesbrough
| Played | Won | Drawn | Lost | For | Against | TTL Att | AVG Att | |
| Home | 1 | 1 | 0 | 0 | 3 | 2 | 28,597 | 28,597 |
| Away / Neutral | 2 | 1 | 0 | 1 | 3 | 2 | 108,123 | 54,062 |
| Total | 3 | 2 | 0 | 1 | 6 | 4 | 136,720 | 45,573 |
| Games since last league cup defeat: | Home: 1 | Away: 1 | All: 2 |
| Games since last league cup draw: | Home: 1 | Away: 2 | All: 3 |
| Games since last league cup win: | Home: 0 | Away: 0 | All: 0 |
| 30 Chelsea players have made League Cup Appearances against Middlesbrough
| 6 Chelsea players have scored League Cup Goals against Middlesbrough
|
Other Competitive Matches versus Middlesbrough
(Full member's cup, Charity & Community Shield and World Club Cup matches)
| Played | Won | Drawn | Lost | For | Against | TTL Att | AVG Att | |
| Home | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Away / Neutral | 1 | 1 | 0 | 0 | 1 | 0 | 76,369 | 76,369 |
| Total | 1 | 1 | 0 | 0 | 1 | 0 | 76,369 | 76,369 |
| Games since last O.C. defeat: | Home: 0 | Away: 1 | All: 1 |
| Games since last O.C. draw: | Home: 0 | Away: 1 | All: 1 |
| Games since last O.C. win: | Home: 0 | Away: 0 | All: 0 |
| 18 Chelsea players have made Other Competitive Appearances against Middlesbrough
| 2 Chelsea players have scored Other Competitive Goals against Middlesbrough
|
All competitive Matches versus Middlesbrough
| Played | Won | Drawn | Lost | For | Against | TTL Att | AVG Att | |
| Home | 55 | 37 | 13 | 5 | 106 | 39 | 1,768,987 | 32,163 |
| Away | 60 | 19 | 16 | 25 | 72 | 85 | 1,556,423 | 25,940 |
| Total | 115 | 56 | 29 | 30 | 178 | 124 | 3,325,410 | 28,917 |
| 392 Chelsea players have made Competitive Appearances against Middlesbrough
| 106 Chelsea players have scored Competitive Goals against Middlesbrough
|
Match Listing v Middlesbrough
| Comp | Date | Home | Away | Att | |||
| League | 26th Dec 1907 | Chelsea | 1 | 0 | Middlesbrough | 40,000 |  |
| League | 1st Jan 1908 | Middlesbrough | 3 | 1 | Chelsea | 30,000 |  |
| League | 1st Jan 1909 | Middlesbrough | 1 | 4 | Chelsea | 25,000 | |
| League | 9th Apr 1909 | Chelsea | 3 | 0 | Middlesbrough | 50,000 | |
| League | 9th Oct 1909 | Middlesbrough | 0 | 1 | Chelsea | 12,000 | |
| League | 19th Feb 1910 | Chelsea | 2 | 1 | Middlesbrough | 20,000 | |
| League | 14th Dec 1912 | Chelsea | 2 | 3 | Middlesbrough | 35,000 | |
| League | 19th Apr 1913 | Middlesbrough | 0 | 3 | Chelsea | 8,000 | |
| League | 1st Nov 1913 | Chelsea | 3 | 2 | Middlesbrough | 40,000 | |
| League | 7th Mar 1914 | Middlesbrough | 2 | 0 | Chelsea | 14,000 | |
| League | 19th Sep 1914 | Middlesbrough | 3 | 0 | Chelsea | 12,000 | |
| League | 23rd Jan 1915 | Chelsea | 2 | 2 | Middlesbrough | 7,500 |  |
| League | 22nd Nov 1919 | Middlesbrough | 0 | 0 | Chelsea | 20,000 | |
| League | 29th Nov 1919 | Chelsea | 3 | 1 | Middlesbrough | 50,000 | |
| League | 23rd Apr 1921 | Middlesbrough | 0 | 0 | Chelsea | 20,000 | |
| League | 30th Apr 1921 | Chelsea | 1 | 1 | Middlesbrough | 30,000 | |
| League | 26th Dec 1921 | Middlesbrough | 0 | 1 | Chelsea | 30,000 | |
| League | 27th Dec 1921 | Chelsea | 1 | 1 | Middlesbrough | 67,000 | |
| League | 9th Sep 1922 | Chelsea | 1 | 1 | Middlesbrough | 40,000 | |
| League | 16th Sep 1922 | Middlesbrough | 2 | 1 | Chelsea | 20,000 | |
| League | 17th Nov 1923 | Middlesbrough | 2 | 0 | Chelsea | 10,000 | |
| League | 24th Nov 1923 | Chelsea | 2 | 0 | Middlesbrough | 18,000 | |
| League | 13th Dec 1924 | Chelsea | 2 | 0 | Middlesbrough | 22,000 | |
| League | 18th Apr 1925 | Middlesbrough | 1 | 1 | Chelsea | 14,000 | |
| League | 12th Dec 1925 | Middlesbrough | 1 | 2 | Chelsea | 14,395 | |
| League | 24th Apr 1926 | Chelsea | 0 | 1 | Middlesbrough | 25,552 | |
| League | 28th Aug 1926 | Chelsea | 3 | 0 | Middlesbrough | 29,849 | |
| League | 15th Jan 1927 | Middlesbrough | 0 | 0 | Chelsea | 23,964 | |
| League | 8th Sep 1928 | Chelsea | 2 | 0 | Middlesbrough | 48,775 | |
| League | 19th Jan 1929 | Middlesbrough | 4 | 5 | Chelsea | 24,768 | |
| League | 4th Oct 1930 | Chelsea | 4 | 0 | Middlesbrough | 48,395 | |
| League | 7th Feb 1931 | Middlesbrough | 2 | 2 | Chelsea | 16,443 | |
| League | 29th Aug 1931 | Middlesbrough | 0 | 2 | Chelsea | 24,510 | |
| League | 2nd Jan 1932 | Chelsea | 4 | 0 | Middlesbrough | 25,259 | |
| League | 8th Oct 1932 | Chelsea | 2 | 1 | Middlesbrough | 18,181 | |
| League | 1st Mar 1933 | Middlesbrough | 2 | 1 | Chelsea | 8,219 | |
| League | 14th Oct 1933 | Chelsea | 2 | 3 | Middlesbrough | 16,078 | |
| League | 24th Feb 1934 | Middlesbrough | 2 | 2 | Chelsea | 12,962 | |
| League | 22nd Dec 1934 | Chelsea | 2 | 1 | Middlesbrough | 23,724 | |
| League | 4th May 1935 | Middlesbrough | 2 | 2 | Chelsea | 17,505 | |
| League | 9th Nov 1935 | Chelsea | 2 | 1 | Middlesbrough | 33,408 | |
| League | 4th Mar 1936 | Middlesbrough | 4 | 1 | Chelsea | 7,968 | |
| League | 12th Sep 1936 | Middlesbrough | 2 | 0 | Chelsea | 21,278 | |
| League | 9th Jan 1937 | Chelsea | 1 | 0 | Middlesbrough | 30,201 | |
| League | 18th Sep 1937 | Middlesbrough | 4 | 3 | Chelsea | 19,631 | |
| League | 29th Jan 1938 | Chelsea | 0 | 1 | Middlesbrough | 27,081 | |
| League | 10th Sep 1938 | Middlesbrough | 1 | 1 | Chelsea | 28,359 | |
| League | 14th Jan 1939 | Chelsea | 4 | 2 | Middlesbrough | 26,750 | |
| League | 5th Oct 1946 | Middlesbrough | 3 | 2 | Chelsea | 44,082 | |
| League | 10th May 1947 | Chelsea | 2 | 0 | Middlesbrough | 22,482 | |
| League | 18th Oct 1947 | Chelsea | 4 | 2 | Middlesbrough | 49,398 | |
| League | 6th Mar 1948 | Middlesbrough | 0 | 0 | Chelsea | 28,174 | |
| League | 21st Aug 1948 | Chelsea | 1 | 0 | Middlesbrough | 60,981 | |
| League | 18th Dec 1948 | Middlesbrough | 1 | 1 | Chelsea | 23,464 | |
| League | 26th Nov 1949 | Middlesbrough | 2 | 1 | Chelsea | 24,815 | |
| League | 29th Mar 1950 | Chelsea | 2 | 1 | Middlesbrough | 15,513 | |
| League | 26th Aug 1950 | Middlesbrough | 3 | 0 | Chelsea | 41,573 | |
| League | 23rd Dec 1950 | Chelsea | 1 | 1 | Middlesbrough | 35,313 | |
| League | 6th Oct 1951 | Middlesbrough | 0 | 0 | Chelsea | 30,010 | |
| League | 16th Feb 1952 | Chelsea | 5 | 0 | Middlesbrough | 37,805 | |
| League | 29th Nov 1952 | Middlesbrough | 4 | 0 | Chelsea | 19,683 | |
| League | 18th Apr 1953 | Chelsea | 1 | 1 | Middlesbrough | 40,042 | |
| League | 17th Oct 1953 | Chelsea | 1 | 1 | Middlesbrough | 23,513 | |
| League | 6th Mar 1954 | Middlesbrough | 3 | 3 | Chelsea | 27,920 | |
| League | 20th Oct 1962 | Chelsea | 3 | 2 | Middlesbrough | 32,551 | |
| League | 9th Mar 1963 | Middlesbrough | 1 | 0 | Chelsea | 24,781 | |
| League Cup | 13th Sep 1967 | Middlesbrough | 2 | 1 | Chelsea | 30,425 | |
| League Cup | 7th Oct 1970 | Chelsea | 3 | 2 | Middlesbrough | 28,597 | |
| League | 7th Sep 1974 | Middlesbrough | 1 | 1 | Chelsea | 25,480 | |
| League | 22nd Mar 1975 | Chelsea | 1 | 2 | Middlesbrough | 22,240 | |
| League | 15th Oct 1977 | Chelsea | 0 | 0 | Middlesbrough | 21,091 | |
| League | 4th Apr 1978 | Middlesbrough | 2 | 0 | Chelsea | 15,288 | |
| League | 16th Dec 1978 | Middlesbrough | 7 | 2 | Chelsea | 15,107 | |
| League | 21st Apr 1979 | Chelsea | 2 | 1 | Middlesbrough | 12,007 | |
| League | 11th Dec 1982 | Middlesbrough | 3 | 1 | Chelsea | 8,836 | |
| League | 14th May 1983 | Chelsea | 0 | 0 | Middlesbrough | 19,340 | |
| League | 24th Sep 1983 | Chelsea | 0 | 0 | Middlesbrough | 15,822 | |
| League | 2nd Jan 1984 | Middlesbrough | 2 | 1 | Chelsea | 11,579 | |
| League Playoff | 25th May 1988 | Middlesbrough | 2 | 0 | Chelsea | 25,531 | |
| League Playoff | 28th May 1988 | Chelsea | 1 | 0 | Middlesbrough | 40,550 | |
| Full Members Cup | 25th Mar 1990 | Middlesbrough | 0 | 1 | Chelsea | 76,369 | |
| League | 11th Dec 1992 | Middlesbrough | 0 | 0 | Chelsea | 15,599 | |
| F.A. Cup | 13th Jan 1993 | Middlesbrough | 2 | 1 | Chelsea | 16,776 | |
| League | 3rd Apr 1993 | Chelsea | 4 | 0 | Middlesbrough | 13,043 | |
| League | 26th Aug 1995 | Middlesbrough | 2 | 0 | Chelsea | 28,286 | |
| League | 4th Feb 1996 | Chelsea | 5 | 0 | Middlesbrough | 21,060 | |
| League | 21st Aug 1996 | Chelsea | 1 | 0 | Middlesbrough | 28,272 | |
| League | 22nd Mar 1997 | Middlesbrough | 1 | 0 | Chelsea | 29,811 | |
| F.A. Cup | 17th May 1997 | Middlesbrough | 0 | 2 | Chelsea | 79,160 | |
| League Cup | 29th Mar 1998 | Middlesbrough | 0 | 2 | Chelsea | 77,698 | |
| League | 26th Sep 1998 | Chelsea | 2 | 0 | Middlesbrough | 34,811 | |
| League | 14th Apr 1999 | Middlesbrough | 0 | 0 | Chelsea | 34,406 | |
| League | 25th Sep 1999 | Middlesbrough | 0 | 1 | Chelsea | 34,183 | |
| League | 22nd Apr 2000 | Chelsea | 1 | 1 | Middlesbrough | 34,800 | |
| League | 16th Dec 2000 | Middlesbrough | 1 | 0 | Chelsea | 29,422 | |
| League | 31st Mar 2001 | Chelsea | 2 | 1 | Middlesbrough | 34,933 | |
| League | 23rd Sep 2001 | Chelsea | 2 | 2 | Middlesbrough | 36,767 | |
| League | 27th Apr 2002 | Middlesbrough | 0 | 2 | Chelsea | 28,686 | |
| League | 16th Nov 2002 | Chelsea | 1 | 0 | Middlesbrough | 39,064 | |
| League | 14th Dec 2002 | Middlesbrough | 1 | 1 | Chelsea | 29,160 | |
| F.A. Cup | 4th Jan 2003 | Chelsea | 1 | 0 | Middlesbrough | 29,796 | |
| League | 5th Oct 2003 | Middlesbrough | 1 | 2 | Chelsea | 29,170 | |
| League | 10th Apr 2004 | Chelsea | 0 | 0 | Middlesbrough | 40,873 | |
| League | 25th Sep 2004 | Middlesbrough | 0 | 1 | Chelsea | 32,341 | |
| League | 4th Jan 2005 | Chelsea | 2 | 0 | Middlesbrough | 40,982 | |
| League | 3rd Dec 2005 | Chelsea | 1 | 0 | Middlesbrough | 41,666 | |
| League | 11th Feb 2006 | Middlesbrough | 3 | 0 | Chelsea | 31,037 | |
| League | 23rd Aug 2006 | Middlesbrough | 2 | 1 | Chelsea | 29,198 | |
| League | 10th Feb 2007 | Chelsea | 3 | 0 | Middlesbrough | 41,699 | |
| League | 20th Oct 2007 | Middlesbrough | 0 | 2 | Chelsea | 27,699 | |
| League | 30th Mar 2008 | Chelsea | 1 | 0 | Middlesbrough | 39,993 | |
| League | 18th Oct 2008 | Middlesbrough | 0 | 5 | Chelsea | 29,221 | |
| League | 28th Jan 2009 | Chelsea | 2 | 0 | Middlesbrough | 40,280 | |
| F.A. Cup | 27th Feb 2013 | Middlesbrough | 0 | 2 | Chelsea | 27,856 | |
| League | 20th Nov 2016 | Middlesbrough | 0 | 1 | Chelsea | 32,704 | |
| League | 8th May 2017 | Chelsea | 3 | 0 | Middlesbrough | 41,500 | |
| F.A. Cup | 19th Mar 2022 | Middlesbrough | 0 | 2 | Chelsea | 31,422 | |
They played for both
24 players have represented both Chelsea & Middlesbrough during their careers. In approximate chronological order, they are:
| Anthony Barness |
| Billy Brawn |
| Geoff Butler |
| Geremi |
| Jimmy Floyd Hasselbaink |
| George Henderson |
| Robert Huth |
| Tony McAndrew |
| Martin Moran |
| Seamus O'Connell |
| John O'Rourke |
| Andy Townsend |
| Andy Wilson |
| Jimmy Windridge |
| Darren Wood |
| Boudewijn Zenden |
| John Obi Mikel |
| Ross Turnbull |
| Josh McEachran |
| Mark Schwarzer |
| Tomáš Kalas |
| Lewis Baker |
| Nathaniel Chalobah |
| Marcus Bettinelli |
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