This page lists the head-to-head record of Middlesbrough vs Portsmouth including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | Portsmouth | Middlesbrough | Draws |
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| Total Matches | 63 | 25 | 16 | 22 |
| At Fratton Park | 31 | 6 | 11 | 14 |
| At Riverside Stadium | 32 | 19 | 5 | 8 |
| Premier League Matches | 50 | 21 | 14 | 15 |
| Championship Matches | 13 | 4 | 2 | 7 |
| Total Goals Scored | 189 | 100 | 89 | |
Last 50 Portsmouth vs Middlesbrough Matches
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| 2025 4 October | | Championship | Portsmouth | 1 - 0 | Middlesbrough |
| 2025 18 January | | Championship | Portsmouth | 2 - 1 | Middlesbrough |
| 2024 24 August | | Championship | Middlesbrough | 2 - 2 | Portsmouth |
| 2012 3 March | | Championship | Portsmouth | 1 - 3 | Middlesbrough |
| 2011 6 August | | Championship | Middlesbrough | 2 - 2 | Portsmouth |
| 2011 12 March | | Championship | Portsmouth | 0 - 0 | Middlesbrough |
| 2010 2 October | | Championship | Middlesbrough | 2 - 2 | Portsmouth |
| 2009 14 March | | Premier League | Middlesbrough | 1 - 1 | Portsmouth |
| 2008 13 September | | Premier League | Portsmouth | 2 - 1 | Middlesbrough |
| 2008 3 May | | Premier League | Middlesbrough | 2 - 0 | Portsmouth |
| 2007 29 December | | Premier League | Portsmouth | 0 - 1 | Middlesbrough |
| 2007 30 January | | Premier League | Portsmouth | 0 - 0 | Middlesbrough |
| 2006 28 August | | Premier League | Middlesbrough | 0 - 4 | Portsmouth |
| 2006 14 April | | Premier League | Portsmouth | 1 - 0 | Middlesbrough |
| 2005 14 October | | Premier League | Middlesbrough | 1 - 1 | Portsmouth |
| 2005 31 January | | Premier League | Portsmouth | 2 - 1 | Middlesbrough |
| 2004 23 October | | Premier League | Middlesbrough | 1 - 1 | Portsmouth |
| 2004 14 May | | Premier League | Portsmouth | 5 - 1 | Middlesbrough |
| 2003 5 December | | Premier League | Middlesbrough | 0 - 0 | Portsmouth |
| 1998 13 March | | Championship | Portsmouth | 0 - 0 | Middlesbrough |
| 1997 4 November | | Championship | Middlesbrough | 1 - 1 | Portsmouth |
| 1994 2 December | | Championship | Middlesbrough | 4 - 0 | Portsmouth |
| 1994 22 October | | Championship | Portsmouth | 0 - 0 | Middlesbrough |
| 1994 15 April | | Championship | Middlesbrough | 0 - 2 | Portsmouth |
| 1993 1 November | | Championship | Portsmouth | 2 - 0 | Middlesbrough |
| 1954 19 March | | Premier League | Middlesbrough | 2 - 2 | Portsmouth |
| 1953 30 October | | Premier League | Portsmouth | 0 - 2 | Middlesbrough |
| 1953 1 May | | Premier League | Portsmouth | 1 - 4 | Middlesbrough |
| 1952 12 December | | Premier League | Middlesbrough | 3 - 2 | Portsmouth |
| 1952 29 February | | Premier League | Middlesbrough | 2 - 1 | Portsmouth |
| 1951 12 October | | Premier League | Portsmouth | 5 - 4 | Middlesbrough |
| 1950 15 December | | Premier League | Middlesbrough | 3 - 1 | Portsmouth |
| 1950 18 August | | Premier League | Portsmouth | 1 - 1 | Middlesbrough |
| 1949 30 December | | Premier League | Portsmouth | 1 - 1 | Middlesbrough |
| 1949 2 September | | Premier League | Middlesbrough | 1 - 5 | Portsmouth |
| 1948 14 September | | Premier League | Middlesbrough | 1 - 1 | Portsmouth |
| 1948 7 September | | Premier League | Portsmouth | 1 - 0 | Middlesbrough |
| 1948 13 April | | Premier League | Portsmouth | 6 - 1 | Middlesbrough |
| 1947 19 September | | Premier League | Middlesbrough | 1 - 2 | Portsmouth |
| 1947 28 March | | Premier League | Portsmouth | 3 - 1 | Middlesbrough |
| 1946 22 November | | Premier League | Middlesbrough | 3 - 3 | Portsmouth |
| 1939 28 March | | Premier League | Middlesbrough | 8 - 2 | Portsmouth |
| 1938 18 November | | Premier League | Portsmouth | 1 - 1 | Middlesbrough |
| 1938 25 January | | Premier League | Middlesbrough | 0 - 0 | Portsmouth |
| 1937 10 September | | Premier League | Portsmouth | 0 - 2 | Middlesbrough |
| 1937 1 January | | Premier League | Middlesbrough | 2 - 2 | Portsmouth |
| 1936 4 September | | Premier League | Portsmouth | 2 - 1 | Middlesbrough |
| 1935 27 December | | Premier League | Portsmouth | 1 - 0 | Middlesbrough |
| 1935 30 August | | Premier League | Middlesbrough | 3 - 2 | Portsmouth |
| 1934 4 September | | Premier League | Portsmouth | 1 - 0 | Middlesbrough |
Biggest Portsmouth Victory vs Middlesbrough
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| 1948 13 April | | Premier League | Portsmouth | 6 - 1 | Middlesbrough |
Biggest Middlesbrough Victory vs Portsmouth
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| 1939 28 March | | Premier League | Middlesbrough | 8 - 2 | Portsmouth |
Biggest Portsmouth Defeat vs Middlesbrough
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| 1939 28 March | | Premier League | Middlesbrough | 8 - 2 | Portsmouth |
Biggest Middlesbrough Defeat vs Portsmouth
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| 1948 13 April | | Premier League | Portsmouth | 6 - 1 | Middlesbrough |
Last 5 Portsmouth Home Matches
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| 2025 4 October | | Championship | Portsmouth | 1 - 0 | Middlesbrough |
| 2025 1 October | | Championship | Portsmouth | 2 - 2 | Watford |
| 2025 20 September | | Championship | Portsmouth | 0 - 2 | Sheffield Wednesday |
| 2025 30 August | | Championship | Portsmouth | 1 - 0 | Preston North End |
| 2025 16 August | | Championship | Portsmouth | 1 - 2 | Norwich City |
Last 5 Middlesbrough Home Matches
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| 2025 30 September | | Championship | Middlesbrough | 0 - 0 | Stoke City |
| 2025 19 September | | Championship | Middlesbrough | 2 - 1 | West Bromwich Albion |
| 2025 30 August | | Championship | Middlesbrough | 1 - 0 | Sheffield United |
| 2025 12 August | | Carling Cup | Middlesbrough | 0 - 4 | Doncaster Rovers |
| 2025 9 August | | Championship | Middlesbrough | 1 - 0 | Swansea City |
Last 5 Portsmouth Away Matches
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| 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 |
| 2025 9 August | | Championship | Oxford United | 0 - 1 | Portsmouth |
| 2025 26 April | | Championship | Sheffield Wednesday | 1 - 1 | Portsmouth |
Last 5 Middlesbrough Away Matches
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| 2025 4 October | | Championship | Portsmouth | 1 - 0 | Middlesbrough |
| 2025 27 September | | Championship | Southampton | 1 - 1 | Middlesbrough |
| 2025 13 September | | Championship | Preston North End | 2 - 2 | Middlesbrough |
| 2025 23 August | | Championship | Norwich City | 1 - 2 | Middlesbrough |
| 2025 16 August | | Championship | Millwall | 0 - 3 | Middlesbrough |