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| Season 1981-82 |
| Pompey Match Results Season: 1989/90 Division Two | < Prev Season | Next Season > |
| Match Date | Fixture | Opponents (Select for match details) | Result | Score |
| Sat 19 Aug 1989 | A | Watford | L | 0 - 1 |
| Wed 23 Aug 1989 | A | Bristol Rovers - Football League Cup Round 1 1st Leg | L | 0 - 1 |
| Sat 26 Aug 1989 | H | Stoke City | D | 0 - 0 |
| Tue 29 Aug 1989 | H | Bristol Rovers - Football League Cup Round 1 2nd Leg | W | 2 - 0 |
| Sat 2 Sep 1989 | A | Bradford City | D | 1 - 1 |
| Fri 8 Sep 1989 | H | Hull City | D | 2 - 2 |
| Tue 12 Sep 1989 | H | Plymouth Argyle | L | 0 - 3 |
| Sat 16 Sep 1989 | A | Newcastle Utd | L | 0 - 1 |
| Wed 20 Sep 1989 | H | Manchester Utd - Football League Cup Round 2 1st Leg | L | 2 - 3 |
| Sat 23 Sep 1989 | H | Middlesbrough | W | 3 - 1 |
| Tue 26 Sep 1989 | H | West Ham Utd | L | 0 - 1 |
| Sat 30 Sep 1989 | A | Wolverhampton Wanderers | L | 0 - 5 |
| Tue 3 Oct 1989 | A | Manchester Utd - Football League Cup Round 2 2nd Leg | D | 0 - 0 |
| Sat 7 Oct 1989 | A | Oxford Utd | L | 1 - 2 |
| Sat 14 Oct 1989 | H | Blackburn Rovers | D | 1 - 1 |
| Tue 17 Oct 1989 | H | Leeds Utd | D | 3 - 3 |
| Sat 21 Oct 1989 | A | Bournemouth | W | 1 - 0 |
| Sat 28 Oct 1989 | H | Ipswich Town | L | 2 - 3 |
| Tue 31 Oct 1989 | A | Sheffield Utd | L | 1 - 2 |
| Sat 4 Nov 1989 | A | Barnsley | W | 1 - 0 |
| Sat 11 Nov 1989 | H | Port Vale | W | 2 - 0 |
| Sat 18 Nov 1989 | H | West Bromwich Albion | D | 1 - 1 |
| Sun 26 Nov 1989 | A | Swindon Town | D | 2 - 2 |
| Sat 2 Dec 1989 | H | Watford | L | 1 - 2 |
| Tue 5 Dec 1989 | H | Wimbledon - Full Members Cup Round 2 | L | 0 - 1 |
| Sun 10 Dec 1989 | A | Plymouth Argyle | W | 2 - 0 |
| Sat 16 Dec 1989 | H | Sunderland | D | 3 - 3 |
| Tue 26 Dec 1989 | A | Brighton | D | 0 - 0 |
| Sat 30 Dec 1989 | A | Oldham Athletic | D | 3 - 3 |
| Mon 1 Jan 1990 | H | Leicester City | L | 2 - 3 |
| Sat 6 Jan 1990 | A | Crystal Palace - FA Cup Round 3 | L | 1 - 2 |
| Sat 13 Jan 1990 | A | Stoke City | W | 2 - 1 |
| Sat 20 Jan 1990 | H | Bradford City | W | 3 - 0 |
| Sat 3 Feb 1990 | A | Middlesbrough | L | 0 - 2 |
| Sat 10 Feb 1990 | H | Newcastle Utd | D | 1 - 1 |
| Sat 17 Feb 1990 | A | Hull City | W | 2 - 1 |
| Sat 24 Feb 1990 | H | Swindon Town | D | 1 - 1 |
| Sat 3 Mar 1990 | A | West Bromwich Albion | D | 0 - 0 |
| Tue 6 Mar 1990 | H | Wolverhampton Wanderers | L | 1 - 3 |
| Sat 10 Mar 1990 | A | West Ham Utd | L | 1 - 2 |
| Sat 17 Mar 1990 | H | Oxford Utd | W | 2 - 1 |
| Tue 20 Mar 1990 | A | Blackburn Rovers | L | 0 - 2 |
| Sat 24 Mar 1990 | A | Leeds Utd | L | 0 - 2 |
| Sat 31 Mar 1990 | H | Bournemouth | W | 2 - 1 |
| Sat 7 Apr 1990 | H | Sheffield Utd | W | 3 - 2 |
| Tue 10 Apr 1990 | A | Ipswich Town | W | 1 - 0 |
| Sat 14 Apr 1990 | A | Leicester City | D | 1 - 1 |
| Mon 16 Apr 1990 | H | Brighton | W | 3 - 0 |
| Sat 21 Apr 1990 | A | Sunderland | D | 2 - 2 |
| Tue 24 Apr 1990 | H | Oldham Athletic | W | 2 - 1 |
| Sat 28 Apr 1990 | A | Port Vale | D | 1 - 1 |
| Sat 5 May 1990 | H | Barnsley | W | 2 - 1 |
| < Back < League Table < Playing Squad 1989-90 |
