This page lists the head-to-head record of Middlesbrough vs Chelsea including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | Chelsea | Middlesbrough | Draws |
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| Total Matches | 94 | 45 | 24 | 25 |
| At Stamford Bridge | 48 | 14 | 20 | 14 |
| At Riverside Stadium | 46 | 31 | 4 | 11 |
| FA Cup Matches | 2 | 2 | 0 | 0 |
| Premier League Matches | 92 | 43 | 24 | 25 |
| Total Goals Scored | 250 | 147 | 103 | |
Last 50 Chelsea vs Middlesbrough Matches
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| 2022 19 March | | FA Cup | Middlesbrough | 0 - 2 | Chelsea |
| 2017 8 May | | Premier League | Chelsea | 3 - 0 | Middlesbrough |
| 2016 20 November | | Premier League | Middlesbrough | 0 - 1 | Chelsea |
| 2013 27 February | | FA Cup | Middlesbrough | 0 - 2 | Chelsea |
| 2009 28 January | | Premier League | Chelsea | 2 - 0 | Middlesbrough |
| 2008 18 October | | Premier League | Middlesbrough | 0 - 5 | Chelsea |
| 2008 30 March | | Premier League | Chelsea | 1 - 0 | Middlesbrough |
| 2007 20 October | | Premier League | Middlesbrough | 0 - 2 | Chelsea |
| 2007 10 February | | Premier League | Chelsea | 3 - 0 | Middlesbrough |
| 2006 23 August | | Premier League | Middlesbrough | 2 - 1 | Chelsea |
| 2006 10 February | | Premier League | Middlesbrough | 3 - 0 | Chelsea |
| 2005 2 December | | Premier League | Chelsea | 1 - 0 | Middlesbrough |
| 2005 3 January | | Premier League | Chelsea | 2 - 0 | Middlesbrough |
| 2004 24 September | | Premier League | Middlesbrough | 0 - 1 | Chelsea |
| 2004 9 April | | Premier League | Chelsea | 0 - 0 | Middlesbrough |
| 2003 4 October | | Premier League | Middlesbrough | 1 - 2 | Chelsea |
| 2002 13 December | | Premier League | Middlesbrough | 1 - 1 | Chelsea |
| 2002 15 November | | Premier League | Chelsea | 1 - 0 | Middlesbrough |
| 2002 26 April | | Premier League | Middlesbrough | 0 - 2 | Chelsea |
| 2001 22 September | | Premier League | Chelsea | 2 - 2 | Middlesbrough |
| 2001 30 March | | Premier League | Chelsea | 2 - 1 | Middlesbrough |
| 2000 15 December | | Premier League | Middlesbrough | 1 - 0 | Chelsea |
| 2000 21 April | | Premier League | Chelsea | 1 - 1 | Middlesbrough |
| 1999 24 September | | Premier League | Middlesbrough | 0 - 1 | Chelsea |
| 1999 13 April | | Premier League | Middlesbrough | 0 - 0 | Chelsea |
| 1998 25 September | | Premier League | Chelsea | 2 - 0 | Middlesbrough |
| 1997 21 March | | Premier League | Middlesbrough | 1 - 0 | Chelsea |
| 1996 20 August | | Premier League | Chelsea | 1 - 0 | Middlesbrough |
| 1996 3 February | | Premier League | Chelsea | 5 - 0 | Middlesbrough |
| 1995 25 August | | Premier League | Middlesbrough | 2 - 0 | Chelsea |
| 1993 2 April | | Premier League | Chelsea | 4 - 0 | Middlesbrough |
| 1992 10 December | | Premier League | Middlesbrough | 0 - 0 | Chelsea |
| 1979 20 April | | Premier League | Chelsea | 2 - 1 | Middlesbrough |
| 1978 15 December | | Premier League | Middlesbrough | 7 - 2 | Chelsea |
| 1978 3 April | | Premier League | Middlesbrough | 2 - 0 | Chelsea |
| 1977 14 October | | Premier League | Chelsea | 0 - 0 | Middlesbrough |
| 1975 21 March | | Premier League | Chelsea | 1 - 2 | Middlesbrough |
| 1974 6 September | | Premier League | Middlesbrough | 1 - 1 | Chelsea |
| 1954 5 March | | Premier League | Middlesbrough | 3 - 3 | Chelsea |
| 1953 16 October | | Premier League | Chelsea | 1 - 1 | Middlesbrough |
| 1953 17 April | | Premier League | Chelsea | 1 - 1 | Middlesbrough |
| 1952 28 November | | Premier League | Middlesbrough | 4 - 0 | Chelsea |
| 1952 15 February | | Premier League | Chelsea | 5 - 0 | Middlesbrough |
| 1951 5 October | | Premier League | Middlesbrough | 0 - 0 | Chelsea |
| 1950 22 December | | Premier League | Chelsea | 1 - 1 | Middlesbrough |
| 1950 25 August | | Premier League | Middlesbrough | 3 - 0 | Chelsea |
| 1950 28 March | | Premier League | Chelsea | 2 - 1 | Middlesbrough |
| 1949 25 November | | Premier League | Middlesbrough | 2 - 1 | Chelsea |
| 1948 17 December | | Premier League | Middlesbrough | 1 - 1 | Chelsea |
| 1948 20 August | | Premier League | Chelsea | 1 - 0 | Middlesbrough |
Biggest Chelsea Victory vs Middlesbrough
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| 1952 15 February | | Premier League | Chelsea | 5 - 0 | Middlesbrough |
Biggest Middlesbrough Victory vs Chelsea
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| 1978 15 December | | Premier League | Middlesbrough | 7 - 2 | Chelsea |
Biggest Chelsea Defeat vs Middlesbrough
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| 1978 15 December | | Premier League | Middlesbrough | 7 - 2 | Chelsea |
Biggest Middlesbrough Defeat vs Chelsea
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| 1952 15 February | | Premier League | Chelsea | 5 - 0 | Middlesbrough |
Last 5 Chelsea Home Matches
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| 2023 3 December | | Premier League | Chelsea | 3 - 2 | Brighton & Hove Albion |
| 2023 12 November | | Premier League | Chelsea | 4 - 4 | Manchester City |
| 2023 1 November | | Carling Cup | Chelsea | 2 - 0 | Blackburn Rovers |
| 2023 28 October | | Premier League | Chelsea | 0 - 2 | Brentford |
| 2023 21 October | | Premier League | Chelsea | 2 - 2 | Arsenal |
Last 5 Middlesbrough Home Matches
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| 2023 28 November | | Championship | Middlesbrough | 4 - 0 | Preston North End |
| 2023 11 November | | Championship | Middlesbrough | 1 - 0 | Leicester City |
| 2023 28 October | | Championship | Middlesbrough | 0 - 2 | Stoke City |
| 2023 21 October | | Championship | Middlesbrough | 1 - 0 | Birmingham City |
| 2023 3 October | | Championship | Middlesbrough | 2 - 0 | Cardiff City |
Last 5 Chelsea Away Matches
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| 2023 25 November | | Premier League | Newcastle United | 4 - 1 | Chelsea |
| 2023 6 November | | Premier League | Tottenham Hotspur | 1 - 4 | Chelsea |
| 2023 7 October | | Premier League | Burnley | 1 - 4 | Chelsea |
| 2023 2 October | | Premier League | Fulham | 0 - 2 | Chelsea |
| 2023 17 September | | Premier League | AFC Bournemouth | 0 - 0 | Chelsea |
Last 5 Middlesbrough Away Matches
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| 2023 2 December | | Championship | Leeds United | 3 - 2 | Middlesbrough |
| 2023 25 November | | Championship | Bristol City | 3 - 2 | Middlesbrough |
| 2023 4 November | | Championship | Plymouth Argyle | 3 - 3 | Middlesbrough |
| 2023 31 October | | Carling Cup | Exeter City | 2 - 3 | Middlesbrough |
| 2023 24 October | | Championship | Norwich City | 1 - 2 | Middlesbrough |