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| Season 1988-89 |
| Pompey Match Results Season: 1988/89 Division Two | < Prev Season | Next Season > |
| Match Date | Fixture | Opponents (Select for match details) | Result | Score |
| Sat 27 Aug 1988 | A | Shrewsbury Town | W | 2 - 1 |
| Mon 29 Aug 1988 | H | Leicester City | W | 3 - 0 |
| Sat 3 Sep 1988 | H | Leeds Utd | W | 4 - 0 |
| Sun 11 Sep 1988 | A | Swindon Town | D | 1 - 1 |
| Sat 17 Sep 1988 | H | Hull City | L | 1 - 3 |
| Tue 20 Sep 1988 | A | Stoke City | D | 2 - 2 |
| Sat 24 Sep 1988 | H | Crystal Palace | D | 1 - 1 |
| Tue 27 Sep 1988 | H | Scarborough - Football League Cup Round 2 1st Leg | D | 2 - 2 |
| Sat 1 Oct 1988 | A | Bradford City | L | 1 - 2 |
| Wed 5 Oct 1988 | A | Manchester City | L | 1 - 4 |
| Sat 8 Oct 1988 | H | Oxford Utd | W | 2 - 1 |
| Wed 12 Oct 1988 | A | Scarborough - Football League Cup Round 2 2nd Leg | L | 1 - 3 |
| Sat 15 Oct 1988 | H | Bournemouth | W | 2 - 1 |
| Sat 22 Oct 1988 | A | Walsall | D | 1 - 1 |
| Tue 25 Oct 1988 | A | Ipswich Town | W | 1 - 0 |
| Sat 29 Oct 1988 | H | Oldham Athletic | D | 1 - 1 |
| Sat 5 Nov 1988 | A | Birmingham City | D | 0 - 0 |
| Tue 8 Nov 1988 | H | Hull City - Full Members Cup Round 1 | W | 2 - 1 |
| Sat 12 Nov 1988 | H | Plymouth Argyle | W | 2 - 0 |
| Sat 19 Nov 1988 | H | Barnsley | W | 3 - 0 |
| Sat 26 Nov 1988 | A | Blackburn Rovers | L | 1 - 3 |
| Sat 3 Dec 1988 | H | West Bromwich Albion | D | 0 - 0 |
| Sat 10 Dec 1988 | A | Chelsea | D | 3 - 3 |
| Sat 17 Dec 1988 | H | Brighton | W | 2 - 0 |
| Wed 21 Dec 1988 | A | Middlesbrough - Full Members Cup Round 2 | L | 1 - 2 |
| Mon 26 Dec 1988 | A | Watford | L | 0 - 1 |
| Sat 31 Dec 1988 | A | Sunderland | L | 0 - 4 |
| Mon 2 Jan 1989 | H | Swindon Town | L | 0 - 2 |
| Sat 7 Jan 1989 | H | Swindon Town - FA Cup Round 3 | D | 1 - 1 |
| Tue 10 Jan 1989 | A | Swindon Town - FA Cup Round 3 Replay | L | 0 - 2 |
| Sat 14 Jan 1989 | A | Leicester City | L | 1 - 2 |
| Sat 21 Jan 1989 | H | Shrewsbury Town | W | 2 - 0 |
| Sat 4 Feb 1989 | H | Manchester City | L | 0 - 1 |
| Sat 11 Feb 1989 | A | Oxford Utd | L | 0 - 1 |
| Sat 18 Feb 1989 | H | Walsall | D | 1 - 1 |
| Sat 25 Feb 1989 | A | Bournemouth | L | 0 - 1 |
| Tue 28 Feb 1989 | H | Ipswich Town | L | 0 - 1 |
| Sat 4 Mar 1989 | A | Plymouth Argyle | W | 1 - 0 |
| Sat 11 Mar 1989 | H | Birmingham City | W | 1 - 0 |
| Tue 14 Mar 1989 | A | Oldham Athletic | L | 3 - 5 |
| Sat 18 Mar 1989 | H | Stoke City | D | 0 - 0 |
| Sat 25 Mar 1989 | A | Leeds Utd | L | 0 - 1 |
| Mon 27 Mar 1989 | H | Watford | D | 2 - 2 |
| Sat 1 Apr 1989 | A | Hull City | D | 1 - 1 |
| Wed 5 Apr 1989 | A | Brighton | L | 1 - 2 |
| Sat 8 Apr 1989 | H | Sunderland | W | 2 - 0 |
| Sat 15 Apr 1989 | A | Crystal Palace | L | 0 - 2 |
| Sat 22 Apr 1989 | H | Bradford City | L | 1 - 2 |
| Sat 29 Apr 1989 | H | Blackburn Rovers | L | 1 - 2 |
| Mon 1 May 1989 | A | West Bromwich Albion | L | 0 - 3 |
| Sat 6 May 1989 | A | Barnsley | L | 0 - 1 |
| Sat 13 May 1989 | H | Chelsea | L | 2 - 3 |
| < Back < League Table < Playing Squad 1988-89 |
