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| Season 1986-87 |
| Pompey head to head with Wolverhampton Wanderers since 1938/39 |
| Select and click date for match details |
| Team | Played | Win | Lose | Draw | W % |
| Wolverhampton Wanderers | 71 | 19 | 31 | 21 | 27% |
| Match Date | Fixture | Result | Score | Competition |
| Sat 3 Oct 2009 | A | W | 1 - 0 | Premier League |
| Sat 31 Jan 2004 | H | D | 0 - 0 | Premier League |
| Sat 30 Aug 2003 | A | D | 0 - 0 | Premier League |
| Sat 15 Mar 2003 | H | W | 1 - 0 | Division One |
| Wed 6 Nov 2002 | A | D | 1 - 1 | Division One |
| Thu 17 Jan 2002 | H | L | 2 - 3 | Division One |
| Sat 11 Aug 2001 | A | D | 2 - 2 | Division One |
| Sat 13 Jan 2001 | A | D | 1 - 1 | Division One |
| Mon 28 Aug 2000 | H | W | 3 - 1 | Division One |
| Sat 15 Jan 2000 | H | L | 2 - 3 | Division One |
| Sat 14 Aug 1999 | A | D | 1 - 1 | Division One |
| Sat 3 Apr 1999 | A | L | 0 - 2 | Division One |
| Sat 17 Oct 1998 | H | W | 1 - 0 | Division One |
| Sun 29 Mar 1998 | A | L | 0 - 2 | Division One |
| Tue 9 Dec 1997 | H | W | 3 - 2 | Division One |
| Sun 4 May 1997 | A | W | 1 - 0 | Division One |
| Tue 7 Jan 1997 | A | W | 2 - 1 | FA Cup Round 3 |
| Tue 15 Oct 1996 | H | L | 0 - 2 | Division One |
| Sat 16 Mar 1996 | H | L | 0 - 2 | Division One |
| Sat 30 Dec 1995 | A | D | 2 - 2 | Division One |
| Sun 5 Mar 1995 | A | L | 0 - 1 | Division One |
| Sat 24 Sep 1994 | H | L | 1 - 2 | Division One |
| Tue 15 Mar 1994 | H | W | 3 - 0 | Division One |
| Sat 11 Sep 1993 | A | D | 1 - 1 | Division One |
| Sat 24 Apr 1993 | H | W | 2 - 0 | Division One |
| Sat 17 Oct 1992 | A | D | 1 - 1 | Division One |
| Sat 22 Feb 1992 | A | D | 0 - 0 | Division Two |
| Sat 30 Nov 1991 | H | W | 1 - 0 | Division Two |
| Sat 11 May 1991 | A | L | 1 - 3 | Division Two |
| Sat 3 Nov 1990 | H | D | 0 - 0 | Division Two |
| Tue 6 Mar 1990 | H | L | 1 - 3 | Division Two |
| Sat 30 Sep 1989 | A | L | 0 - 5 | Division Two |
| Sat 2 Mar 1985 | A | D | 0 - 0 | Division Two |
| Sat 27 Oct 1984 | H | L | 0 - 1 | Division Two |
| Sat 25 Feb 1967 | H | L | 2 - 3 | Division Two |
| Sat 8 Oct 1966 | A | L | 1 - 3 | Division Two |
| Sat 23 Apr 1966 | H | W | 2 - 0 | Division Two |
| Sat 27 Nov 1965 | A | L | 2 - 8 | Division Two |
| Tue 12 Jan 1965 | A | L | 2 - 3 | FA Cup Round 3 Replay |
| Sat 9 Jan 1965 | H | D | 0 - 0 | FA Cup Round 3 |
| Sat 27 Dec 1958 | A | L | 0 - 7 | Division One |
| Fri 26 Dec 1958 | H | L | 3 - 5 | Division One |
| Sat 5 Apr 1958 | A | L | 0 - 1 | Division One |
| Sat 25 Jan 1958 | A | L | 1 - 5 | FA Cup Round 4 |
| Sat 9 Nov 1957 | H | D | 1 - 1 | Division One |
| Sat 20 Apr 1957 | H | W | 1 - 0 | Division One |
| Sat 13 Oct 1956 | A | L | 0 - 6 | Division One |
| Wed 31 Aug 1955 | A | L | 1 - 3 | Division One |
| Wed 24 Aug 1955 | H | W | 2 - 1 | Division One |
| Sat 1 Jan 1955 | A | D | 2 - 2 | Division One |
| Sat 28 Aug 1954 | H | D | 0 - 0 | Division One |
| Sat 23 Jan 1954 | H | W | 2 - 0 | Division One |
| Sat 12 Sep 1953 | A | L | 3 - 4 | Division One |
| Sat 6 Apr 1953 | A | L | 1 - 4 | Division One |
| Sat 3 Apr 1953 | H | D | 2 - 2 | Division One |
| Sat 19 Jan 1952 | A | D | 1 - 1 | Division One |
| Sat 15 Sep 1951 | H | L | 2 - 3 | Division One |
| Sat 17 Mar 1951 | A | W | 3 - 2 | Division One |
| Sat 28 Oct 1950 | H | L | 1 - 4 | Division One |
| Sat 18 Feb 1950 | A | L | 0 - 1 | Division One |
| Wed 19 Oct 1949 | A | D | 1 - 1 | FA Community Shield |
| Sat 1 Oct 1949 | H | D | 1 - 1 | Division One |
| Sat 16 Apr 1949 | H | W | 5 - 0 | Division One |
| Sat 23 Oct 1948 | A | L | 0 - 3 | Division One |
| Sat 3 Apr 1948 | H | W | 2 - 0 | Division One |
| Sat 15 Nov 1947 | A | L | 1 - 3 | Division One |
| Sat 3 May 1947 | H | D | 1 - 1 | Division One |
| Sat 28 Sep 1946 | A | L | 1 - 3 | Division One |
| Sat 29 Apr 1939 | A | W | 4 - 1 | FA Cup Final - Wembley Stadium |
| Sat 28 Jan 1939 | A | L | 0 - 3 | Division One |
| Sat 24 Sep 1938 | H | W | 1 - 0 | Division One |
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