| Date | Opponents | Type | Res/KO | Venue |
|---|---|---|---|---|
| Sat 27 Aug 1988 | Shrewsbury Town | League | W 2-1 | Gay Meadow |
| Mon 29 Aug 1988 | LEICESTER CITY | League | W 3-0 | Fratton Park |
| Sat 03 Sep 1988 | LEEDS UNITED | League | W 4-0 | Fratton Park |
| Sun 11 Sep 1988 | Swindon Town | League | D 1-1 | County Ground |
| Sat 17 Sep 1988 | HULL CITY | League | L 1-3 | Fratton Park |
| Tue 20 Sep 1988 | Stoke City | League | D 2-2 | Victoria Ground |
| Sat 24 Sep 1988 | CRYSTAL PALACE | League | D 1-1 | Fratton Park |
| Tue 27 Sep 1988 | SCARBOROUGH | League Cup | D 2-2 | Fratton Park |
| Sat 01 Oct 1988 | Bradford City | League | L 1-2 | Valley Parade |
| Wed 05 Oct 1988 | Manchester City | League | L 1-4 | Maine Road |
| Sat 08 Oct 1988 | OXFORD UNITED | League | W 2-1 | Fratton Park |
| Wed 12 Oct 1988 | Scarborough | League Cup | L 1-3* | Athletic Ground |
| Sat 15 Oct 1988 | AFC BOURNEMOUTH | League | W 2-1 | Fratton Park |
| Sat 22 Oct 1988 | Walsall | League | D 1-1 | Fellows Park |
| Tue 25 Oct 1988 | Ipswich Town | League | W 1-0 | Portman Road |
| Sat 29 Oct 1988 | OLDHAM ATHLETIC | League | D 1-1 | Fratton Park |
| Sat 05 Nov 1988 | Birmingham City | League | D 0-0 | St. Andrews |
| Sat 12 Nov 1988 | PLYMOUTH ARGYLE | League | W 2-0 | Fratton Park |
| Sat 19 Nov 1988 | BARNSLEY | League | W 3-0 | Fratton Park |
| Sat 26 Nov 1988 | Blackburn Rovers | League | L 1-3 | Ewood Park |
| Sat 03 Dec 1988 | WEST BROMWICH ALBION | League | D 0-0 | Fratton Park |
| Sat 10 Dec 1988 | Chelsea | League | D 3-3 | Stamford Bridge |
| Sat 17 Dec 1988 | BRIGHTON & HOVE ALBION | League | W 2-0 | Fratton Park |
| Mon 26 Dec 1988 | Watford | League | L 0-1 | Vicarage Road |
| Sat 31 Dec 1988 | Sunderland | League | L 0-4 | Roker Park |
| Mon 02 Jan 1989 | SWINDON TOWN | League | L 0-2 | Fratton Park |
| Sat 07 Jan 1989 | SWINDON TOWN | F.A. Cup | D 1-1 | Fratton Park |
| Tue 10 Jan 1989 | Swindon Town | F.A. Cup | L 0-2 | County Ground |
| Sat 14 Jan 1989 | Leicester City | League | L 1-2 | Filbert Street |
| Sat 21 Jan 1989 | SHREWSBURY TOWN | League | W 2-0 | Fratton Park |
| Sat 04 Feb 1989 | MANCHESTER CITY | League | L 0-1 | Fratton Park |
| Sat 11 Feb 1989 | Oxford United | League | L 0-1 | Manor Ground |
| Sat 18 Feb 1989 | WALSALL | League | D 1-1 | Fratton Park |
| Sat 25 Feb 1989 | AFC Bournemouth | League | L 0-1 | Dean Court |
| Tue 28 Feb 1989 | IPSWICH TOWN | League | L 0-1 | Fratton Park |
| Sat 04 Mar 1989 | Plymouth Argyle | League | W 1-0 | Home Park |
| Sat 11 Mar 1989 | BIRMINGHAM CITY | League | W 1-0 | Fratton Park |
| Tue 14 Mar 1989 | Oldham Athletic | League | L 3-5 | Boundary Park |
| Sat 18 Mar 1989 | STOKE CITY | League | D 0-0 | Fratton Park |
| Sat 25 Mar 1989 | Leeds United | League | L 0-1 | Elland Road |
| Mon 27 Mar 1989 | WATFORD | League | D 2-2 | Fratton Park |
| Sat 01 Apr 1989 | Hull City | League | D 1-1 | Boothferry Park |
| Wed 05 Apr 1989 | Brighton & Hove Albion | League | L 1-2 | Goldstone Ground |
| Sat 08 Apr 1989 | SUNDERLAND | League | W 2-0 | Fratton Park |
| Sat 15 Apr 1989 | Crystal Palace | League | L 0-2 | Selhurst Park |
| Sat 22 Apr 1989 | BRADFORD CITY | League | L 1-2 | Fratton Park |
| Sat 29 Apr 1989 | BLACKBURN ROVERS | League | L 1-2 | Fratton Park |
| Mon 01 May 1989 | West Bromwich Albion | League | L 0-3 | The Hawthorns |
| Sat 06 May 1989 | Barnsley | League | L 0-1 | Oakwell |
| Sat 13 May 1989 | CHELSEA | League | L 2-3 | Fratton Park |
*Scarborough won 5-3 on aggregate