This page lists the head-to-head record of Portsmouth vs Chelsea including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | Chelsea | Portsmouth | Draws |
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| Total Matches | 63 | 31 | 17 | 15 |
| At Stamford Bridge | 31 | 12 | 12 | 7 |
| At Fratton Park | 32 | 19 | 5 | 8 |
| FA Cup Matches | 2 | 2 | 0 | 0 |
| Carling Cup Matches | 1 | 1 | 0 | 0 |
| Premier League Matches | 60 | 28 | 17 | 15 |
| Total Goals Scored | 203 | 117 | 86 | |
Last 50 Chelsea vs Portsmouth Matches
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| 2012 8 January | | FA Cup | Chelsea | 4 - 0 | Portsmouth |
| 2010 15 May | | FA Cup | Chelsea | 1 - 0 | Portsmouth |
| 2010 24 March | | Premier League | Portsmouth | 0 - 5 | Chelsea |
| 2009 16 December | | Premier League | Chelsea | 2 - 1 | Portsmouth |
| 2009 3 March | | Premier League | Portsmouth | 0 - 1 | Chelsea |
| 2008 24 September | | Carling Cup | Portsmouth | 0 - 4 | Chelsea |
| 2008 17 August | | Premier League | Chelsea | 4 - 0 | Portsmouth |
| 2008 2 February | | Premier League | Portsmouth | 1 - 1 | Chelsea |
| 2007 25 August | | Premier League | Chelsea | 1 - 0 | Portsmouth |
| 2007 3 March | | Premier League | Portsmouth | 0 - 2 | Chelsea |
| 2006 21 October | | Premier League | Chelsea | 2 - 1 | Portsmouth |
| 2006 24 February | | Premier League | Chelsea | 2 - 0 | Portsmouth |
| 2005 25 November | | Premier League | Portsmouth | 0 - 2 | Chelsea |
| 2005 21 January | | Premier League | Chelsea | 3 - 0 | Portsmouth |
| 2004 27 December | | Premier League | Portsmouth | 0 - 2 | Chelsea |
| 2004 10 February | | Premier League | Portsmouth | 0 - 2 | Chelsea |
| 2003 27 December | | Premier League | Chelsea | 3 - 0 | Portsmouth |
| 1988 22 January | | Premier League | Chelsea | 0 - 0 | Portsmouth |
| 1987 17 August | | Premier League | Portsmouth | 0 - 3 | Chelsea |
| 1959 16 January | | Premier League | Chelsea | 2 - 2 | Portsmouth |
| 1958 5 September | | Premier League | Portsmouth | 2 - 2 | Chelsea |
| 1957 25 December | | Premier League | Portsmouth | 3 - 0 | Chelsea |
| 1957 24 December | | Premier League | Chelsea | 7 - 4 | Portsmouth |
| 1957 8 February | | Premier League | Portsmouth | 2 - 2 | Chelsea |
| 1956 28 September | | Premier League | Chelsea | 3 - 3 | Portsmouth |
| 1955 30 December | | Premier League | Portsmouth | 4 - 4 | Chelsea |
| 1955 2 September | | Premier League | Chelsea | 1 - 5 | Portsmouth |
| 1955 15 April | | Premier League | Portsmouth | 0 - 0 | Chelsea |
| 1954 26 November | | Premier League | Chelsea | 4 - 1 | Portsmouth |
| 1953 1 September | | Premier League | Portsmouth | 3 - 2 | Chelsea |
| 1953 24 August | | Premier League | Chelsea | 4 - 3 | Portsmouth |
| 1953 2 January | | Premier League | Portsmouth | 2 - 0 | Chelsea |
| 1952 29 August | | Premier League | Chelsea | 2 - 0 | Portsmouth |
| 1951 28 December | | Premier League | Chelsea | 1 - 1 | Portsmouth |
| 1951 31 August | | Premier League | Portsmouth | 1 - 0 | Chelsea |
| 1950 25 December | | Premier League | Chelsea | 1 - 4 | Portsmouth |
| 1950 24 December | | Premier League | Portsmouth | 1 - 3 | Chelsea |
| 1950 24 March | | Premier League | Portsmouth | 4 - 0 | Chelsea |
| 1949 4 November | | Premier League | Chelsea | 1 - 4 | Portsmouth |
| 1948 26 December | | Premier League | Portsmouth | 5 - 2 | Chelsea |
| 1948 24 December | | Premier League | Chelsea | 1 - 2 | Portsmouth |
| 1948 30 April | | Premier League | Portsmouth | 2 - 1 | Chelsea |
| 1947 12 December | | Premier League | Chelsea | 1 - 0 | Portsmouth |
| 1947 25 May | | Premier League | Chelsea | 0 - 3 | Portsmouth |
| 1946 18 October | | Premier League | Portsmouth | 0 - 2 | Chelsea |
| 1939 21 April | | Premier League | Chelsea | 1 - 0 | Portsmouth |
| 1938 16 December | | Premier League | Portsmouth | 2 - 1 | Chelsea |
| 1938 11 February | | Premier League | Chelsea | 3 - 1 | Portsmouth |
| 1937 1 October | | Premier League | Portsmouth | 2 - 4 | Chelsea |
| 1937 5 February | | Premier League | Portsmouth | 4 - 1 | Chelsea |
Biggest Chelsea Victory vs Portsmouth
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| 2010 24 March | | Premier League | Portsmouth | 0 - 5 | Chelsea |
Biggest Portsmouth Victory vs Chelsea
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| 1955 2 September | | Premier League | Chelsea | 1 - 5 | Portsmouth |
Biggest Chelsea Defeat vs Portsmouth
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| 1955 2 September | | Premier League | Chelsea | 1 - 5 | Portsmouth |
Biggest Portsmouth Defeat vs Chelsea
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| 2010 24 March | | Premier League | Portsmouth | 0 - 5 | Chelsea |
Last 5 Chelsea Home Matches
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| 2025 4 May | | Premier League | Chelsea | 3 - 1 | Liverpool |
| 2025 26 April | | Premier League | Chelsea | 1 - 0 | Everton |
| 2025 17 April | | Europa Conference League | Chelsea | 1 - 2 | Legia Warszawa |
| 2025 13 April | | Premier League | Chelsea | 2 - 2 | Ipswich Town |
| 2025 3 April | | Premier League | Chelsea | 1 - 0 | Tottenham Hotspur |
Last 5 Portsmouth Home Matches
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| 2025 3 May | | Championship | Portsmouth | 1 - 1 | Hull City |
| 2025 21 April | | Championship | Portsmouth | 1 - 0 | Watford |
| 2025 12 April | | Championship | Portsmouth | 2 - 2 | Derby County |
| 2025 29 March | | Championship | Portsmouth | 1 - 0 | Blackburn Rovers |
| 2025 12 March | | Championship | Portsmouth | 1 - 2 | Plymouth Argyle |
Last 5 Chelsea Away Matches
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| 2025 1 May | | Europa Conference League | Djurgarden | 1 - 4 | Chelsea |
| 2025 20 April | | Premier League | Fulham | 1 - 2 | Chelsea |
| 2025 10 April | | Europa Conference League | Legia Warszawa | 0 - 3 | Chelsea |
| 2025 6 April | | Premier League | Brentford | 0 - 0 | Chelsea |
| 2025 16 March | | Premier League | Arsenal | 1 - 0 | Chelsea |
Last 5 Portsmouth Away Matches
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| 2025 26 April | | Championship | Sheffield Wednesday | 1 - 1 | Portsmouth |
| 2025 18 April | | Championship | Norwich City | 3 - 5 | Portsmouth |
| 2025 9 April | | Championship | Coventry City | 1 - 0 | Portsmouth |
| 2025 5 April | | Championship | Millwall | 2 - 1 | Portsmouth |
| 2025 15 March | | Championship | Preston North End | 2 - 1 | Portsmouth |