This page lists the head-to-head record of Chelsea vs Portsmouth including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | Portsmouth | Chelsea | Draws |
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| Total Matches | 63 | 17 | 31 | 15 |
| At Fratton Park | 32 | 5 | 19 | 8 |
| At Stamford Bridge | 31 | 12 | 12 | 7 |
| FA Cup Matches | 2 | 0 | 2 | 0 |
| Carling Cup Matches | 1 | 0 | 1 | 0 |
| Premier League Matches | 60 | 17 | 28 | 15 |
| Total Goals Scored | 203 | 86 | 117 | |
Last 50 Portsmouth vs Chelsea 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 Portsmouth Victory vs Chelsea
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| 1955 2 September | | Premier League | Chelsea | 1 - 5 | Portsmouth |
Biggest Chelsea Victory vs Portsmouth
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| 2010 24 March | | Premier League | Portsmouth | 0 - 5 | Chelsea |
Biggest Portsmouth Defeat vs Chelsea
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| 2010 24 March | | Premier League | Portsmouth | 0 - 5 | Chelsea |
Biggest Chelsea Defeat vs Portsmouth
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| 1955 2 September | | Premier League | Chelsea | 1 - 5 | Portsmouth |
Last 5 Portsmouth Home Matches
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| 2025 5 November | | Championship | Portsmouth | 0 - 0 | Wrexham |
| 2025 25 October | | Championship | Portsmouth | 0 - 1 | Stoke City |
| 2025 21 October | | Championship | Portsmouth | 1 - 2 | Coventry City |
| 2025 4 October | | Championship | Portsmouth | 1 - 0 | Middlesbrough |
| 2025 1 October | | Championship | Portsmouth | 2 - 2 | Watford |
Last 5 Chelsea Home Matches
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| 2025 25 October | | Premier League | Chelsea | 1 - 2 | Sunderland |
| 2025 22 October | | UEFA Champions League | Chelsea | 5 - 1 | Ajax |
| 2025 4 October | | Premier League | Chelsea | 2 - 1 | Liverpool |
| 2025 30 September | | UEFA Champions League | Chelsea | 1 - 0 | Benfica |
| 2025 27 September | | Premier League | Chelsea | 1 - 3 | Brighton & Hove Albion |
Last 5 Portsmouth Away Matches
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| 2025 1 November | | Championship | Birmingham City | 4 - 0 | Portsmouth |
| 2025 18 October | | Championship | Leicester City | 1 - 1 | Portsmouth |
| 2025 27 September | | Championship | Ipswich Town | 2 - 1 | Portsmouth |
| 2025 14 September | | Championship | Southampton | 0 - 0 | Portsmouth |
| 2025 23 August | | Championship | West Bromwich Albion | 1 - 1 | Portsmouth |
Last 5 Chelsea Away Matches
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| 2025 5 November | | UEFA Champions League | Qarabagh | 2 - 2 | Chelsea |
| 2025 1 November | | Premier League | Tottenham Hotspur | 0 - 1 | Chelsea |
| 2025 29 October | | Carling Cup | Wolverhampton Wanderers | 3 - 4 | Chelsea |
| 2025 18 October | | Premier League | Nottingham Forest | 0 - 3 | Chelsea |
| 2025 23 September | | Carling Cup | Lincoln City | 1 - 2 | Chelsea |