FA Cup 2023/24, First Round Proper |
| 05.11.2023 | | Chesterfield | | Portsmouth | | 1:0 (1:0) |
| Chesterfield |
FA Cup 2022/23, Third Round Proper |
| 07.01.2023 | | Tottenham Hotspur | | Portsmouth | | 1:0 (0:0) |
| London |
FA Cup 2021/22, Second Round Proper |
| 04.12.2021 | | Portsmouth | | Harrogate Town | | 1:2 (1:1) |
| Portsmouth |
FA Cup 2020/21, Third Round Proper |
| 10.01.2021 | | Bristol City | | Portsmouth | | 2:1 (1:1) * |
| Bristol |
FA Cup 2019/20, Fifth Round Proper |
| 02.03.2020 | | Portsmouth | | Arsenal | | 0:2 (0:1) |
| Portsmouth |
FA Cup 2018/19, Fourth Round Proper |
| 05.02.2019 | | Queens Park Rangers | | Portsmouth | | 2:0 (0:0) * |
| London |
FA Cup 2017/18, First Round Proper |
| 04.11.2017 | | Luton Town | | Portsmouth | | 1:0 (1:0) |
| Luton |
FA Cup 2016/17, First Round Proper |
| 05.11.2016 | | Portsmouth | | Wycombe Wanderers | | 1:2 (0:1) |
| Portsmouth |
FA Cup 2015/16, Fourth Round Proper |
| 30.01.2016 | | Portsmouth | | AFC Bournemouth | | 1:2 (1:0) |
| Portsmouth |
FA Cup 2014/15, First Round Proper |
| 19.11.2014 | | Aldershot Town | | Portsmouth | | 1:0 (0:0) * |
| Aldershot |
FA Cup 2013/14, First Round Proper |
| 09.11.2013 | | Stevenage | | Portsmouth | | 2:1 (2:0) |
| Stevenage |
FA Cup 2012/13, First Round Proper |
| 03.11.2012 | | Portsmouth | | Notts County | | 0:2 (0:1) |
| Portsmouth |
FA Cup 2011/12, Third Round Proper |
| 08.01.2012 | | Chelsea | | Portsmouth | | 4:0 (0:0) |
| London |
FA Cup 2010/11, Third Round Proper |
| 08.01.2011 | | Brighton & Hove Albion | | Portsmouth | | 3:1 (2:0) |
| Brighton & Hove |
FA Cup 2009/10, Final |
| 15.05.2010 | | Chelsea | | Portsmouth | | 1:0 (0:0) |
| London |
FA Cup 2008/09, Fourth Round Proper |
| 24.01.2009 | | Portsmouth | | Swansea City | | 0:2 (0:2) |
| Portsmouth |
FA Cup 2006/07, Fourth Round Proper |
| 27.01.2007 | | Manchester United | | Portsmouth | | 2:1 (0:0) |
| Manchester |
FA Cup 2005/06, Fourth Round Proper |
| 29.01.2006 | | Portsmouth | | Liverpool | | 1:2 (0:2) |
| Portsmouth |
FA Cup 2004/05, Fourth Round Proper |
| 29.01.2005 | | Southampton | | Portsmouth | | 2:1 (0:0) |
| Southampton |
FA Cup 2003/04, Sixth Round Proper |
| 06.03.2004 | | Portsmouth | | Arsenal | | 1:5 (0:3) |
| Portsmouth |
FA Cup 2002/03, Third Round Proper |
| 04.01.2003 | | Manchester United | | Portsmouth | | 4:1 (2:1) |
| Manchester |
FA Cup 2001/02, Third Round Proper |
| 05.01.2002 | | Portsmouth | | Leyton Orient | | 1:4 (1:0) |
| Portsmouth |
FA Cup 2000/01, Third Round Proper |
| 06.01.2001 | | Portsmouth | | Tranmere Rovers | | 1:2 (1:1) |
| Portsmouth |
FA Cup 1999/00, Third Round Proper |
| 11.12.1999 | | Sunderland | | Portsmouth | | 1:0 (1:0) |
| Sunderland |
FA Cup 1998/99, Fourth Round Proper |
| 23.01.1999 | | Portsmouth | | Leeds United | | 1:5 (1:2) |
| Portsmouth |
FA Cup 1997/98, Third Round Proper |
| 14.01.1998 | | Aston Villa | | Portsmouth | | 1:0 (1:0) * |
| Birmingham |
FA Cup 1996/97, Sixth Round Proper |
| 09.03.1997 | | Portsmouth | | Chelsea | | 1:4 (0:2) |
| Portsmouth |
FA Cup 1995/96, Third Round Proper |
| 07.01.1996 | | Southampton | | Portsmouth | | 3:0 (1:0) |
| Southampton |
FA Cup 1994/95, Fourth Round Proper |
| 28.01.1995 | | Portsmouth | | Leicester City | | 0:1 (0:1) |
| Portsmouth |
FA Cup 1993/94, Third Round Proper |
| 19.01.1994 | | Portsmouth | | Blackburn Rovers | | 1:3 (0:1) * |
| Portsmouth |
FA Cup 1992/93, Third Round Proper |
| 02.01.1993 | | Brighton & Hove Albion | | Portsmouth | | 1:0 (1:0) |
| Hove |
FA Cup 1990/91, Fifth Round Proper |
| 16.02.1991 | | Portsmouth | | Tottenham Hotspur | | 1:2 |
| Portsmouth |
FA Cup 1989/90, Third Round Proper |
| 06.01.1990 | | Crystal Palace | | Portsmouth | | 2:1 |
| London |
FA Cup 1988/89, Third Round Proper |
| 10.01.1989 | | Swindon Town | | Portsmouth | | 2:0 (0:0) * |
| Swindon |
FA Cup 1987/88, Sixth Round Proper |
| 12.03.1988 | | Luton Town | | Portsmouth | | 3:1 (2:1) |
| Luton |
FA Cup 1986/87, Fourth Round Proper |
| 31.01.1987 | | Wimbledon | | Portsmouth | | 4:0 |
| London |
FA Cup 1985/86, Third Round Proper |
| 13.01.1986 | | Aston Villa | | Portsmouth | | 3:2 * |
| |
FA Cup 1984/85, Third Round Proper |
| 26.01.1985 | | Blackburn Rovers | | Portsmouth | | 2:1 * |
| |
FA Cup 1983/84, Fourth Round Proper |
| 28.01.1984 | | Portsmouth | | Southampton | | 0:1 |
| |
FA Cup 1982/83, Second Round Proper |
| 11.12.1982 | | Portsmouth | | Aldershot | | 1:3 |
| |
FA Cup 1981/82, First Round Proper |
| 25.11.1981 | | Millwall | | Portsmouth | | 3:2 * |
| |
FA Cup 1980/81, First Round Proper |
| 22.11.1980 | | Colchester United | | Portsmouth | | 3:0 |
| |
FA Cup 1979/80, Third Round Proper |
| 14.01.1980 | | Middlesbrough | | Portsmouth | | 3:0 * |
| |
FA Cup 1978/79, Second Round Proper |
| 16.12.1978 | | Portsmouth | | Reading | | 0:1 |
| |
FA Cup 1977/78, Second Round Proper |
| 20.12.1977 | | Swansea City | | Portsmouth | | 2:1 * |
| |
FA Cup 1976/77, Third Round Proper |
| 08.01.1977 | | Birmingham City | | Portsmouth | | 1:0 |
| Birmingham |
FA Cup 1975/76, Fourth Round Proper |
| 27.01.1976 | | Portsmouth | | Charlton Athletic | | 0:3 * |
| |
FA Cup 1974/75, Third Round Proper |
| 03.01.1975 | | Notts County | | Portsmouth | | 3:1 |
| |
FA Cup 1973/74, Fifth Round Proper |
| 17.02.1974 | | Nottingham Forest | | Portsmouth | | 1:0 |
| |
FA Cup 1972/73, Third Round Proper |
| 16.01.1973 | | Bristol City | | Portsmouth | | 4:1 * |
| |
FA Cup 1971/72, Fifth Round Proper |
| 26.02.1972 | | Birmingham City | | Portsmouth | | 3:1 |
| |
FA Cup 1970/71, Fourth Round Proper |
| 01.02.1971 | | Arsenal | | Portsmouth | | 3:2 * |
| London |
FA Cup 1969/70, Third Round Proper |
| 03.01.1970 | | Portsmouth | | Tranmere Rovers | | 1:2 (1:1) |
| |
FA Cup 1968/69, Fourth Round Proper |
| 25.01.1969 | | Blackburn Rovers | | Portsmouth | | 4:0 |
| |
FA Cup 1967/68, Fifth Round Proper |
| 09.03.1968 | | Portsmouth | | West Bromwich Albion | | 1:2 |
| |
FA Cup 1966/67, Fourth Round Proper |
| 18.02.1967 | | Tottenham Hotspur | | Portsmouth | | 3:1 |
| |
FA Cup 1965/66, Third Round Proper |
| 26.01.1966 | | Portsmouth | | Grimsby Town | | 1:3 * |
| |
FA Cup 1964/65, Third Round Proper |
| 12.01.1965 | | Wolverhampton Wanderers | | Portsmouth | | 3:2 * |
| |
FA Cup 1963/64, Third Round Proper |
| 04.01.1964 | | Stoke City | | Portsmouth | | 4:1 |
| |
FA Cup 1962/63, Fourth Round Proper |
| 19.03.1963 | | Portsmouth | | Coventry City | | 1:2 * |
| |
FA Cup 1961/62, First Round Proper |
| 04.11.1961 | | Crystal Palace | | Portsmouth | | 3:0 |
| |
FA Cup 1960/61, Third Round Proper |
| 07.01.1961 | | Portsmouth | | Peterborough United | | 1:2 |
| |
FA Cup 1959/60, Third Round Proper |
| 09.01.1960 | | Sheffield United | | Portsmouth | | 3:0 |
| |
FA Cup 1958/59, Fifth Round Proper |
| 14.02.1959 | | Burnley | | Portsmouth | | 1:0 |
| |
FA Cup 1957/58, Fourth Round Proper |
| 25.01.1958 | | Wolverhampton Wanderers | | Portsmouth | | 5:1 |
| |
FA Cup 1956/57, Fourth Round Proper |
| 26.01.1957 | | Portsmouth | | Nottingham Forest | | 1:3 |
| |
FA Cup 1955/56, Fourth Round Proper |
| 28.01.1956 | | West Bromwich Albion | | Portsmouth | | 2:0 |
| |
FA Cup 1954/55, Third Round Proper |
| 08.01.1955 | | Bristol Rovers | | Portsmouth | | 2:1 |
| |
FA Cup 1953/54, Fifth Round Proper |
| 24.02.1954 | | Portsmouth | | Bolton Wanderers | | 1:2 * |
| |
FA Cup 1952/53, Third Round Proper |
| 13.01.1953 | | Burnley | | Portsmouth | | 3:1 * |
| |
FA Cup 1951/52, Sixth Round Proper |
| 08.03.1952 | | Portsmouth | | Newcastle United | | 2:4 |
| |
FA Cup 1950/51, Third Round Proper |
| 06.01.1951 | | Luton Town | | Portsmouth | | 2:0 |
| |
FA Cup 1949/50, Fifth Round Proper |
| 15.02.1950 | | Portsmouth | | Manchester United | | 1:3 * |
| |
FA Cup 1948/49, Semi Final |
| 26.03.1949 | | Leicester City | | Portsmouth | | 3:1 (1:1) |
| London |
FA Cup 1947/48, Fourth Round Proper |
| 24.01.1948 | | Portsmouth | | Preston North End | | 1:3 |
| |
FA Cup 1946/47, Fourth Round Proper |
| 25.01.1947 | | Birmingham City | | Portsmouth | | 1:0 |
| |
FA Cup 1945/46, Third Round Proper |
| 05.01.1946 | | Birmingham City | | Portsmouth | | 1:0 |
| |
FA Cup 1937/38, Fourth Round Proper |
| 22.01.1938 | | Brentford | | Portsmouth | | 2:1 |
| |
FA Cup 1936/37, Third Round Proper |
| 16.01.1937 | | Portsmouth | | Tottenham Hotspur | | 0:5 |
| |
FA Cup 1935/36, Third Round Proper |
| 11.01.1936 | | Manchester City | | Portsmouth | | 3:1 |
| |
FA Cup 1934/35, Fourth Round Proper |
| 30.01.1935 | | Bristol City | | Portsmouth | | 2:0 * |
| |
FA Cup 1933/34, Final |
| 28.04.1934 | | Manchester City | | Portsmouth | | 2:1 (0:1) |
| London |
FA Cup 1932/33, Third Round Proper |
| 14.01.1933 | | Grimsby Town | | Portsmouth | | 3:2 |
| |
FA Cup 1931/32, Fifth Round Proper |
| 13.02.1932 | | Portsmouth | | Arsenal | | 0:2 |
| |
FA Cup 1930/31, Fifth Round Proper |
| 14.02.1931 | | Portsmouth | | West Bromwich Albion | | 0:1 |
| |
FA Cup 1929/30, Fourth Round Proper |
| 25.01.1930 | | Portsmouth | | Brighton & Hove Albion | | 0:1 |
| |
FA Cup 1928/29, Final |
| 27.04.1929 | | Bolton Wanderers | | Portsmouth | | 2:0 (0:0) |
| London |
FA Cup 1927/28, Third Round Proper |
| 14.01.1928 | | Portsmouth | | West Ham United | | 0:2 |
| |
FA Cup 1926/27, Fourth Round Proper |
| 29.01.1927 | | Reading | | Portsmouth | | 3:1 |
| |
FA Cup 1925/26, Third Round Proper |
| 18.01.1926 | | Derby County | | Portsmouth | | 2:0 * |
| |
FA Cup 1924/25, Second Round Proper |
| 09.02.1925 | | Blackburn Rovers | | Portsmouth | | 1:0 * |
| |
FA Cup 1923/24, First Round Proper |
| 12.01.1924 | | Portsmouth | | Newcastle United | | 2:4 |
| |
FA Cup 1922/23, First Round Proper |
| 17.01.1923 | | Leeds United | | Portsmouth | | 3:1 * |
| |
FA Cup 1921/22, First Round Proper |
| 11.01.1922 | | Luton Town | | Portsmouth | | 2:1 * |
| |
FA Cup 1920/21, First Round Proper |
| 08.01.1921 | | South Shields | | Portsmouth | | 3:0 |
| |
FA Cup 1919/20, First Round Proper |
| 17.01.1920 | | Bradford City | | Portsmouth | | 2:0 |
| |
FA Cup 1914/15, First Round Proper |
| 09.01.1915 | | Bradford Park Avenue | | Portsmouth | | 1:0 |
| |
FA Cup 1913/14, First Round Proper |
| 10.01.1914 | | Portsmouth | | Exeter City | | 0:4 |
| |
FA Cup 1912/13, First Round Proper |
| 15.01.1913 | | Portsmouth | | Brighton & Hove Albion | | 1:2 |
| |
FA Cup 1911/12, Second Round Proper |
| 03.02.1912 | | Bradford Park Avenue | | Portsmouth | | 2:0 |
| |
FA Cup 1910/11, First Round Proper |
| 14.01.1911 | | Portsmouth | | Aston Villa | | 1:4 |
| |
FA Cup 1909/10, Second Round Proper |
| 05.02.1910 | | Portsmouth | | Coventry City | | 0:1 |
| |
FA Cup 1908/09, Second Round Proper |
| 11.02.1909 | | Sheffield Wednesday | | Portsmouth | | 3:0 * |
| |
FA Cup 1907/08, Third Round Proper |
| 22.02.1908 | | Portsmouth | | Stoke | | 0:1 |
| |
FA Cup 1906/07, Second Round Proper |
| 02.02.1907 | | Barnsley | | Portsmouth | | 1:0 |
| |
FA Cup 1905/06, First Round Proper |
| 13.01.1906 | | Southampton | | Portsmouth | | 5:1 |
| |
FA Cup 1904/05, Second Round Proper |
| 18.02.1905 | | Sheffield Wednesday | | Portsmouth | | 2:1 |
| |
FA Cup 1903/04, First Round Proper |
| 06.02.1904 | | Portsmouth | | Derby County | | 2:5 |
| |
FA Cup 1902/03, First Round Proper |
| 07.02.1903 | | Everton | | Portsmouth | | 5:0 |
| |
FA Cup 1901/02, Third Round Proper |
| 27.02.1902 | | Derby County | | Portsmouth | | 6:3 * |
| |
FA Cup 1900/01, Intermediate Round |
| 05.01.1901 | | Newton Heath | | Portsmouth | | 3:0 |
| |
FA Cup 1899/00, First Round Proper |
| 05.02.1900 | | Blackburn Rovers | | Portsmouth | | 5:0 * |
| |