| Date | Opponents | Type | Res/KO | Venue |
|---|---|---|---|---|
| Sat 19 Aug 1989 | Watford | League | L 0-1 | Vicarage Road |
| Wed 23 Aug 1989 | Bristol Rovers | League Cup | L 0-1 | Twerton Park |
| Sat 26 Aug 1989 | STOKE CITY | League | D 0-0 | Fratton Park |
| Tue 29 Aug 1989 | BRISTOL ROVERS | League Cup | W 2-0* | Fratton Park |
| Sat 02 Sep 1989 | Bradford City | League | D 1-1 | Valley Parade |
| Sat 09 Sep 1989 | HULL CITY | League | D 2-2 | Fratton Park |
| Tue 12 Sep 1989 | PLYMOUTH ARGYLE | League | L 0-3 | Fratton Park |
| Sat 16 Sep 1989 | Newcastle United | League | L 0-1 | St. James Park |
| Wed 20 Sep 1989 | MANCHESTER UNITED | League Cup | L 2-3 | Fratton Park |
| Sat 23 Sep 1989 | MIDDLESBROUGH | League | W 3-1 | Fratton Park |
| Tue 26 Sep 1989 | WEST HAM UNITED | League | L 0-1 | Fratton Park |
| Sat 30 Sep 1989 | Wolverhampton Wanderers | League | L 0-5 | Molineux |
| Tue 03 Oct 1989 | Manchester United | League Cup | D 0-0** | Old Trafford |
| Sat 07 Oct 1989 | Oxford United | League | L 1-2 | Manor Ground |
| Sat 14 Oct 1989 | BLACKBURN ROVERS | League | D 1-1 | Fratton Park |
| Tue 17 Oct 1989 | LEEDS UNITED | League | D 3-3 | Fratton Park |
| Sat 21 Oct 1989 | AFC Bournemouth | League | W 1-0 | Dean Court |
| Sat 28 Oct 1989 | IPSWICH TOWN | League | L 2-3 | Fratton Park |
| Tue 31 Oct 1989 | Sheffield United | League | L 1-2 | Bramall Lane |
| Sat 04 Nov 1989 | Barnsley | League | W 1-0 | Oakwell |
| Sat 11 Nov 1989 | PORT VALE | League | W 2-0 | Fratton Park |
| Sat 18 Nov 1989 | WEST BROMWICH ALBION | League | D 1-1 | Fratton Park |
| Sun 26 Nov 1989 | Swindon Town | League | D 2-2 | County Ground |
| Sat 02 Dec 1989 | WATFORD | League | L 1-2 | Fratton Park |
| Sun 10 Dec 1989 | Plymouth Argyle | League | W 2-0 | Home Park |
| Sat 16 Dec 1989 | SUNDERLAND | League | D 3-3 | Fratton Park |
| Tue 26 Dec 1989 | Brighton & Hove Albion | League | D 0-0 | Goldstone Ground |
| Sat 30 Dec 1989 | Oldham Athletic | League | D 3-3 | Boundary Park |
| Mon 01 Jan 1990 | LEICESTER CITY | League | L 2-3 | Fratton Park |
| Sat 06 Jan 1990 | Crystal Palace | F.A. Cup | L 1-2 | Selhurst Park |
| Sat 13 Jan 1990 | Stoke City | League | W 2-1 | Victoria Ground |
| Sat 20 Jan 1990 | BRADFORD CITY | League | W 3-0 | Fratton Park |
| Sat 03 Feb 1990 | Middlesbrough | League | L 0-2 | Ayresome Park |
| Sat 10 Feb 1990 | NEWCASTLE UNITED | League | D 1-1 | Fratton Park |
| Sat 17 Feb 1990 | Hull City | League | W 2-1 | Boothferry Park |
| Sat 24 Feb 1990 | SWINDON TOWN | League | D 1-1 | Fratton Park |
| Sat 03 Mar 1990 | West Bromwich Albion | League | D 0-0 | The Hawthorns |
| Tue 06 Mar 1990 | WOLVERHAMPTON WANDERERS | League | L 1-3 | Fratton Park |
| Sat 10 Mar 1990 | West Ham United | League | L 1-2 | Boleyn Ground |
| Sat 17 Mar 1990 | OXFORD UNITED | League | W 2-1 | Fratton Park |
| Tue 20 Mar 1990 | Blackburn Rovers | League | L 0-2 | Ewood Park |
| Sat 24 Mar 1990 | Leeds United | League | L 0-2 | Elland Road |
| Sat 31 Mar 1990 | AFC BOURNEMOUTH | League | W 2-1 | Fratton Park |
| Sat 07 Apr 1990 | SHEFFIELD UNITED | League | W 3-2 | Fratton Park |
| Tue 10 Apr 1990 | Ipswich Town | League | W 1-0 | Portman Road |
| Sat 14 Apr 1990 | Leicester City | League | D 1-1 | Filbert Street |
| Mon 16 Apr 1990 | BRIGHTON & HOVE ALBION | League | W 3-0 | Fratton Park |
| Sat 21 Apr 1990 | Sunderland | League | D 2-2 | Roker Park |
| Tue 24 Apr 1990 | OLDHAM ATHLETIC | League | W 2-1 | Fratton Park |
| Sat 28 Apr 1990 | Port Vale | League | D 1-1 | Vale Park |
| Sat 05 May 1990 | BARNSLEY | League | W 2-1 | Fratton Park |
* Portsmouth won 2-1 on aggregate
** Manchester United won 3-2 on aggregate