Wed 21 Dec 1988
Full Members Cup Round 2
Middlesbrough 2 Pompey 1
| Pos | Player | Goals | Subs |
| 1 | Andy Gosney | ||
| 2 | Lee Sandford | ||
| 3 | Paul Hardyman | ||
| 4 | Eamonn Collins | ||
| 5 | Kit Symons | ||
| 6 | Cive Whitehead | ||
| 7 | Mark Chamberlain | ||
| 8 | Mickey Ross | * | |
| 8 | Shaun Gale | s | |
| 9 | Darryl Powell | 1 | * |
| 9 | Lee Russell | s | |
| 10 | Mike Fillery | ||
| 11 | Mark Kelly |
| Select Pompey player for stats |
| Scorers: Powell Manager: Alan Ball Attendance: 6,853 |
Season 1988/89
Fixtures
Select opponent for Pompey line-up Change Season
| Date | Opponent | Result | Score |
| Sat 27 Aug 1988 | Shrewsbury Town A | W | 2 - 1 |
| Mon 29 Aug 1988 | Leicester City H | W | 3 - 0 |
| Sat 3 Sep 1988 | Leeds United H | W | 4 - 0 |
| Sun 11 Sep 1988 | Swindon Town A | D | 1 - 1 |
| Sat 17 Sep 1988 | Hull City H | L | 1 - 3 |
| Tue 20 Sep 1988 | Stoke City A | D | 2 - 2 |
| Sat 24 Sep 1988 | Crystal Palace H | D | 1 - 1 |
| Tue 27 Sep 1988 | Scarborough- Football League Cup Round 2 1st Leg H | D | 2 - 2 |
| Sat 1 Oct 1988 | Bradford City A | L | 1 - 2 |
| Wed 5 Oct 1988 | Manchester City A | L | 1 - 4 |
| Sat 8 Oct 1988 | Oxford United H | W | 2 - 1 |
| Wed 12 Oct 1988 | Scarborough- Football League Cup Round 2 2nd Leg A | L | 1 - 3 |
| Sat 15 Oct 1988 | AFC Bournemouth H | W | 2 - 1 |
| Sat 22 Oct 1988 | Walsall A | D | 1 - 1 |
| Tue 25 Oct 1988 | Ipswich Town A | W | 1 - 0 |
| Sat 29 Oct 1988 | Oldham Athletic H | D | 1 - 1 |
| Sat 5 Nov 1988 | Birmingham City A | D | 0 - 0 |
| Tue 8 Nov 1988 | Hull City- Full Members Cup Round 1 H | W | 2 - 1 |
| Sat 12 Nov 1988 | Plymouth Argyle H | W | 2 - 0 |
| Sat 19 Nov 1988 | Barnsley H | W | 3 - 0 |
| Sat 26 Nov 1988 | Blackburn Rovers A | L | 1 - 3 |
| Sat 3 Dec 1988 | West Bromwich Albion H | D | 0 - 0 |
| Sat 10 Dec 1988 | Chelsea A | D | 3 - 3 |
| Sat 17 Dec 1988 | Brighton and Hove Albion H | W | 2 - 0 |
| Wed 21 Dec 1988 | Middlesbrough- Full Members Cup Round 2 A | L | 1 - 2 |
| Mon 26 Dec 1988 | Watford A | L | 0 - 1 |
| Sat 31 Dec 1988 | Sunderland A | L | 0 - 4 |
| Mon 2 Jan 1989 | Swindon Town H | L | 0 - 2 |
| Sat 7 Jan 1989 | Swindon Town- FA Cup Round 3 H | D | 1 - 1 |
| Tue 10 Jan 1989 | Swindon Town- FA Cup Round 3 Replay A | L | 0 - 2 |
| Sat 14 Jan 1989 | Leicester City A | L | 1 - 2 |
| Sat 21 Jan 1989 | Shrewsbury Town H | W | 2 - 0 |
| Sat 4 Feb 1989 | Manchester City H | L | 0 - 1 |
| Sat 11 Feb 1989 | Oxford United A | L | 0 - 1 |
| Sat 18 Feb 1989 | Walsall H | D | 1 - 1 |
| Sat 25 Feb 1989 | AFC Bournemouth A | L | 0 - 1 |
| Tue 28 Feb 1989 | Ipswich Town H | L | 0 - 1 |
| Sat 4 Mar 1989 | Plymouth Argyle A | W | 1 - 0 |
| Sat 11 Mar 1989 | Birmingham City H | W | 1 - 0 |
| Tue 14 Mar 1989 | Oldham Athletic A | L | 3 - 5 |
| Sat 18 Mar 1989 | Stoke City H | D | 0 - 0 |
| Sat 25 Mar 1989 | Leeds United A | L | 0 - 1 |
| Mon 27 Mar 1989 | Watford H | D | 2 - 2 |
| Sat 1 Apr 1989 | Hull City A | D | 1 - 1 |
| Wed 5 Apr 1989 | Brighton and Hove Albion A | L | 1 - 2 |
| Sat 8 Apr 1989 | Sunderland H | W | 2 - 0 |
| Sat 15 Apr 1989 | Crystal Palace A | L | 0 - 2 |
| Sat 22 Apr 1989 | Bradford City H | L | 1 - 2 |
| Sat 29 Apr 1989 | Blackburn Rovers H | L | 1 - 2 |
| Mon 1 May 1989 | West Bromwich Albion A | L | 0 - 3 |
| Sat 6 May 1989 | Barnsley A | L | 0 - 1 |
| Sat 13 May 1989 | Chelsea H | L | 2 - 3 |
