Sat 1 Nov 1958
Division One
Birmingham City 2 Pompey 2
| Pos | Player | Goals |
| 1 | Norman Uprichard | |
| 2 | Tommy McGhee | |
| 3 | Alex Wilson | |
| 4 | John Phillips | |
| 5 | Jimmy Dickinson | |
| 6 | Tom Casey | |
| 7 | Reg Cutler | 1 |
| 8 | Harry Harris | |
| 9 | Ron Newman | |
| 10 | Ron Saunders | 1 |
| 11 | Michael Barnard |
| Select Pompey player for stats |
| Scorers: Saunders, Cutler Manager: Freddie Cox Attendance: 23,695 |
Season 1958/59
Fixtures
Select opponent for Pompey line-up Change Season
| Date | Opponent | Result | Score |
| Sat 23 Aug 1958 | West Ham United H | L | 1 - 2 |
| Mon 25 Aug 1958 | Aston Villa A | L | 2 - 3 |
| Sat 30 Aug 1958 | Nottingham Forest A | L | 0 - 5 |
| Wed 3 Sep 1958 | Aston Villa H | W | 5 - 2 |
| Sat 6 Sep 1958 | Chelsea H | D | 2 - 2 |
| Wed 10 Sep 1958 | West Bromwich Albion A | W | 2 - 1 |
| Sat 13 Sep 1958 | Blackpool A | D | 1 - 1 |
| Wed 17 Sep 1958 | West Bromwich Albion H | L | 2 - 6 |
| Sat 20 Sep 1958 | Blackburn Rovers H | W | 2 - 1 |
| Sat 27 Sep 1958 | Newcastle United A | L | 0 - 2 |
| Sat 4 Oct 1958 | Tottenham Hotspur H | D | 1 - 1 |
| Sat 11 Oct 1958 | Leeds United H | W | 2 - 0 |
| Sat 18 Oct 1958 | Manchester City A | L | 2 - 3 |
| Sat 25 Oct 1958 | Luton Town H | D | 2 - 2 |
| Sat 1 Nov 1958 | Birmingham City A | D | 2 - 2 |
| Mon 3 Nov 1958 | Luton Town- Southern Floodlight League Cup Round 1 H | L | 0 - 2 |
| Sat 8 Nov 1958 | Leicester City H | W | 4 - 1 |
| Sat 15 Nov 1958 | Preston North End A | L | 1 - 3 |
| Sat 22 Nov 1958 | Burnley H | W | 4 - 2 |
| Sat 29 Nov 1958 | Bolton Wanderers A | L | 1 - 2 |
| Sat 6 Dec 1958 | Arsenal H | L | 0 - 1 |
| Sat 13 Dec 1958 | Everton A | L | 1 - 2 |
| Sat 20 Dec 1958 | West Ham United A | L | 0 - 6 |
| Fri 26 Dec 1958 | Wolverhampton Wanderers H | L | 3 - 5 |
| Sat 27 Dec 1958 | Wolverhampton Wanderers A | L | 0 - 7 |
| Sat 3 Jan 1959 | Nottingham Forest H | L | 0 - 1 |
| Sat 10 Jan 1959 | Swansea Town- FA Cup Round 3 H | W | 3 - 1 |
| Sat 17 Jan 1959 | Chelsea A | D | 2 - 2 |
| Sat 24 Jan 1959 | Accrington Stanley- FA Cup Round 4 A | D | 0 - 0 |
| Wed 28 Jan 1959 | Accrington Stanley- FA Cup Round 4 Replay H | W | 4 - 1 |
| Sat 31 Jan 1959 | Blackpool H | L | 1 - 2 |
| Sat 7 Feb 1959 | Blackburn Rovers A | L | 1 - 2 |
| Sat 14 Feb 1959 | Burnley- FA Cup Round 5 A | L | 0 - 1 |
| Sat 21 Feb 1959 | Tottenham Hotspur A | D | 4 - 4 |
| Sat 28 Feb 1959 | Leeds United A | D | 1 - 1 |
| Sat 7 Mar 1959 | Manchester City H | L | 3 - 4 |
| Wed 11 Mar 1959 | Newcastle United H | L | 1 - 5 |
| Sat 21 Mar 1959 | Birmingham City H | D | 1 - 1 |
| Fri 27 Mar 1959 | Manchester United A | L | 1 - 6 |
| Sat 28 Mar 1959 | Leicester City A | L | 1 - 3 |
| Mon 30 Mar 1959 | Manchester United H | L | 1 - 3 |
| Sat 4 Apr 1959 | Preston North End H | L | 1 - 2 |
| Sat 11 Apr 1959 | Burnley A | L | 1 - 2 |
| Wed 15 Apr 1959 | Everton H | L | 2 - 3 |
| Sat 18 Apr 1959 | Bolton Wanderers H | L | 0 - 1 |
| Wed 22 Apr 1959 | Luton Town A | L | 1 - 3 |
| Sat 25 Apr 1959 | Arsenal A | L | 2 - 5 |
