| Date | Opponents | Type | Res/KO | Venue |
|---|---|---|---|---|
| Sat 23 Aug 1986 | Brighton & Hove Albion | League | D 0-0 | Goldstone Ground |
| Sat 30 Aug 1986 | IPSWICH TOWN | League | D 1-1 | Fratton Park |
| Tue 02 Sep 1986 | Hull City | League | W 2-0 | Boothferry Park |
| Sat 06 Sep 1986 | Barnsley | League | W 2-0 | Oakwell |
| Sat 13 Sep 1986 | BLACKBURN ROVERS | League | W 1-0 | Fratton Park |
| Sat 20 Sep 1986 | Stoke City | League | D 1-1 | Victoria Ground |
| Wed 24 Sep 1986 | Wrexham | League Cup | W 2-1 | Racecourse Ground |
| Sat 27 Sep 1986 | HUDDERSFIELD TOWN | League | W 1-0 | Fratton Park |
| Sat 04 Oct 1986 | Sunderland | League | D 0-0 | Roker Park |
| Tue 07 Oct 1986 | WREXHAM | League Cup | W 2-0* | Fratton Park |
| Sat 11 Oct 1986 | BIRMINGHAM CITY | League | W 2-0 | Fratton Park |
| Sat 18 Oct 1986 | Leeds United | League | L 1-3 | Elland Road |
| Tue 21 Oct 1986 | DERBY COUNTY | League | W 3-1 | Fratton Park |
| Sat 25 Oct 1986 | WEST BROMWICH ALBION | League | W 2-1 | Fratton Park |
| Wed 29 Oct 1986 | Bradford City | League Cup | L 1-3 | Valley Parade |
| Sat 01 Nov 1986 | Oldham Athletic | League | D 0-0 | Boundary Park |
| Sat 08 Nov 1986 | BRADFORD CITY | League | W 2-1 | Fratton Park |
| Sat 15 Nov 1986 | Shrewsbury Town | League | L 0-1 | Gay Meadow |
| Sat 22 Nov 1986 | GRIMSBY TOWN | League | W 2-1 | Fratton Park |
| Sat 29 Nov 1986 | Millwall | League | D 1-1 | The Den (old) |
| Sat 06 Dec 1986 | CRYSTAL PALACE | League | W 2-0 | Fratton Park |
| Sat 13 Dec 1986 | Sheffield United | League | L 0-1 | Bramall Lane |
| Sat 20 Dec 1986 | BARNSLEY | League | W 2-1 | Fratton Park |
| Fri 26 Dec 1986 | Plymouth Argyle | League | W 3-2 | Home Park |
| Mon 29 Dec 1986 | SHREWSBURY TOWN | League | W 3-0 | Fratton Park |
| Thu 01 Jan 1987 | READING | League | W 1-0 | Fratton Park |
| Sat 03 Jan 1987 | Blackburn Rovers | League | L 0-1 | Ewood Park |
| Sat 10 Jan 1987 | BLACKBURN ROVERS | F.A. Cup | W 2-0 | Fratton Park |
| Sat 24 Jan 1987 | BRIGHTON & HOVE ALBION | League | W 1-0 | Fratton Park |
| Sat 31 Jan 1987 | Wimbledon | F.A. Cup | L 0-4 | Plough Lane |
| Sat 07 Feb 1987 | Ipswich Town | League | W 1-0 | Portman Road |
| Sat 14 Feb 1987 | HULL CITY | League | W 1-0 | Fratton Park |
| Sat 21 Feb 1987 | Huddersfield Town | League | L 0-2 | Leeds Road |
| Sat 28 Feb 1987 | STOKE CITY | League | W 3-0 | Fratton Park |
| Wed 04 Mar 1987 | Derby County | League | D 0-0 | Baseball Ground |
| Tue 10 Mar 1987 | LEEDS UNITED | League | D 1-1 | Fratton Park |
| Sat 21 Mar 1987 | Birmingham City | League | W 1-0 | St. Andrews |
| Sat 28 Mar 1987 | SUNDERLAND | League | W 3-1 | Fratton Park |
| Sat 04 Apr 1987 | Bradford City | League | L 0-1 | Valley Parade |
| Sat 11 Apr 1987 | OLDHAM ATHLETIC | League | W 3-0 | Fratton Park |
| Sat 18 Apr 1987 | Reading | League | D 2-2 | Elm Park |
| Mon 20 Apr 1987 | PLYMOUTH ARGYLE | League | L 0-1 | Fratton Park |
| Sat 25 Apr 1987 | Grimsby Town | League | W 2-0 | Blundell Park |
| Wed 29 Apr 1987 | West Bromwich Albion | League | L 0-1 | The Hawthorns |
| Sat 02 May 1987 | MILLWALL | League | W 2-0 | Fratton Park |
| Mon 04 May 1987 | Crystal Palace | League | L 0-1 | Selhurst Park |
| Sat 09 May 1987 | SHEFFIELD UNITED | League | L 1-2 | Fratton Park |
* Pompey won 4-1 on aggregate