Sat 3 Sep 1949
Division One
Middlesbrough 1 Pompey 5
| Pos | Player | Goals |
| 1 | Earnie Butler | |
| 2 | Billy Hindmarsh | |
| 3 | Harry Ferrier | |
| 4 | Jimmy Scoular | |
| 5 | Reg Flewin | |
| 6 | Jimmy Dickinson | |
| 7 | Peter Harris | 3 |
| 8 | Lindy Delapenha | |
| 9 | Ike Clarke | 1 |
| 10 | Len Phillips | |
| 11 | Jack Froggatt | 1 |
| Select Pompey player for stats |
| Scorers: Harris 3, Clarke, Froggatt Manager: Bob Jackson Attendance: 45,000 |
Season 1949/50
Fixtures
Select opponent for Pompey line-up Change Season
| Date | Opponent | Result | Score |
| Sat 20 Aug 1949 | Newcastle United A | W | 3 - 1 |
| Wed 24 Aug 1949 | Manchester City H | D | 1 - 1 |
| Sat 27 Aug 1949 | Blackpool H | L | 2 - 3 |
| Wed 31 Aug 1949 | Manchester City A | L | 0 - 1 |
| Sat 3 Sep 1949 | Middlesbrough A | W | 5 - 1 |
| Mon 5 Sep 1949 | Aston Villa A | L | 0 - 1 |
| Sat 10 Sep 1949 | Everton H | W | 7 - 0 |
| Sat 17 Sep 1949 | Huddersfield Town A | W | 1 - 0 |
| Sat 24 Sep 1949 | Bolton Wanderers H | D | 1 - 1 |
| Sat 1 Oct 1949 | Wolverhampton Wanderers H | D | 1 - 1 |
| Sat 8 Oct 1949 | Birmingham City A | W | 3 - 0 |
| Sat 15 Oct 1949 | Derby County H | W | 3 - 1 |
| Wed 19 Oct 1949 | Wolverhampton Wanderers- FA Community Shield N | D | 1 - 1 |
| Sat 22 Oct 1949 | West Bromwich Albion A | L | 0 - 3 |
| Sat 29 Oct 1949 | Manchester United H | D | 0 - 0 |
| Sat 5 Nov 1949 | Chelsea A | W | 4 - 1 |
| Sat 12 Nov 1949 | Stoke City H | D | 0 - 0 |
| Sat 19 Nov 1949 | Burnley A | L | 1 - 2 |
| Sat 26 Nov 1949 | Sunderland H | D | 2 - 2 |
| Sat 3 Dec 1949 | Liverpool A | D | 2 - 2 |
| Sat 10 Dec 1949 | Arsenal H | W | 2 - 1 |
| Sat 17 Dec 1949 | Newcastle United H | W | 1 - 0 |
| Sat 24 Dec 1949 | Blackpool A | L | 1 - 2 |
| Mon 26 Dec 1949 | Charlton Athletic A | W | 2 - 1 |
| Tue 27 Dec 1949 | Charlton Athletic H | W | 1 - 0 |
| Sat 31 Dec 1949 | Middlesbrough H | D | 1 - 1 |
| Sat 7 Jan 1950 | Norwich City- FA Cup Round 3 H | D | 1 - 1 |
| Thu 12 Jan 1950 | Norwich City- FA Cup Round 3 Replay A | W | 2 - 0 |
| Sat 14 Jan 1950 | Everton A | W | 2 - 1 |
| Sat 21 Jan 1950 | Huddersfield Town H | W | 4 - 0 |
| Sat 28 Jan 1950 | Grimsby Town- FA Cup Round 4 H | W | 5 - 0 |
| Sat 4 Feb 1950 | Bolton Wanderers A | L | 0 - 1 |
| Sat 11 Feb 1950 | Manchester United- FA Cup Round 5 A | D | 3 - 3 |
| Wed 15 Feb 1950 | Manchester United- FA Cup Round 5 Replay H | L | 1 - 3 |
| Sat 18 Feb 1950 | Wolverhampton Wanderers A | L | 0 - 1 |
| Sat 25 Feb 1950 | Birmingham City H | W | 2 - 0 |
| Wed 8 Mar 1950 | Derby County A | L | 1 - 2 |
| Sat 11 Mar 1950 | Burnley H | W | 2 - 1 |
| Sat 18 Mar 1950 | Sunderland A | D | 1 - 1 |
| Sat 25 Mar 1950 | Chelsea H | W | 4 - 0 |
| Sat 1 Apr 1950 | Stoke City A | W | 1 - 0 |
| Fri 7 Apr 1950 | Fulham H | W | 3 - 0 |
| Sat 8 Apr 1950 | West Bromwich Albion H | L | 0 - 1 |
| Mon 10 Apr 1950 | Fulham A | W | 1 - 0 |
| Sat 15 Apr 1950 | Manchester United A | W | 2 - 0 |
| Sat 22 Apr 1950 | Liverpool H | W | 2 - 1 |
| Wed 3 May 1950 | Arsenal A | L | 0 - 2 |
| Sat 6 May 1950 | Aston Villa H | W | 5 - 1 |
