Mon 23 Aug 1965
Division Two
Preston North End 4 Pompey 1
| Pos | Player | Goals |
| 1 | John Armstrong | |
| 2 | Alex Wilson | |
| 3 | Roy Lunniss | |
| 4 | Johnny Gordon | |
| 5 | Vince Radcliffe | |
| 6 | Harry Harris | |
| 7 | Brian Lewis | |
| 8 | Cliff Portwood | 1 |
| 9 | Ray Hiron | |
| 10 | Albie McCann | |
| 11 | Tony Barton |
| Select Pompey player for stats |
| Scorers: Portwood Manager: George Smith Attendance: 17,952 |
Season 1965/66
Fixtures
Select opponent for Pompey line-up Change Season
| Date | Opponent | Result | Score |
| Sat 21 Aug 1965 | Plymouth Argyle H | W | 4 - 1 |
| Mon 23 Aug 1965 | Preston North End A | L | 1 - 4 |
| Sat 28 Aug 1965 | Southampton A | D | 2 - 2 |
| Wed 1 Sep 1965 | Preston North End H | W | 4 - 1 |
| Sat 4 Sep 1965 | Bolton Wanderers A | L | 0 - 2 |
| Wed 8 Sep 1965 | Crystal Palace A | L | 1 - 4 |
| Sat 11 Sep 1965 | Ipswich Town H | W | 1 - 0 |
| Wed 15 Sep 1965 | Crystal Palace H | D | 1 - 1 |
| Sat 18 Sep 1965 | Birmingham City A | W | 3 - 1 |
| Wed 22 Sep 1965 | Oldham Athletic- Football League Cup Round 2 A | W | 2 - 1 |
| Sat 25 Sep 1965 | Leyton Orient H | W | 4 - 1 |
| Sat 9 Oct 1965 | Derby County H | D | 1 - 1 |
| Wed 13 Oct 1965 | Cardiff City- Football League Cup Round 3 A | L | 0 - 2 |
| Sat 16 Oct 1965 | Cardiff City A | W | 2 - 1 |
| Sat 23 Oct 1965 | Carlisle United H | W | 4 - 1 |
| Tue 26 Oct 1965 | Middlesbrough A | L | 2 - 5 |
| Sat 30 Oct 1965 | Coventry City A | L | 2 - 3 |
| Sat 6 Nov 1965 | Bristol City H | L | 2 - 4 |
| Sat 13 Nov 1965 | Manchester City A | L | 1 - 3 |
| Sat 20 Nov 1965 | Rotherham United H | D | 1 - 1 |
| Sat 27 Nov 1965 | Wolverhampton Wanderers A | L | 2 - 8 |
| Sat 4 Dec 1965 | Norwich City H | L | 0 - 3 |
| Sat 11 Dec 1965 | Bury A | L | 0 - 1 |
| Sat 18 Dec 1965 | Cardiff City H | W | 3 - 1 |
| Mon 27 Dec 1965 | Charlton Athletic A | D | 2 - 2 |
| Tue 28 Dec 1965 | Charlton Athletic H | W | 3 - 1 |
| Sat 1 Jan 1966 | Derby County A | L | 1 - 3 |
| Sat 8 Jan 1966 | Manchester City H | D | 2 - 2 |
| Sat 15 Jan 1966 | Carlisle United A | L | 1 - 2 |
| Sat 22 Jan 1966 | Grimsby Town- FA Cup Round 3 A | D | 0 - 0 |
| Wed 26 Jan 1966 | Grimsby Town- FA Cup Round 3 Replay H | L | 1 - 3 |
| Sat 29 Jan 1966 | Plymouth Argyle A | L | 1 - 3 |
| Sat 5 Feb 1966 | Southampton H | L | 2 - 5 |
| Sat 19 Feb 1966 | Bolton Wanderers H | W | 1 - 0 |
| Sat 26 Feb 1966 | Ipswich Town A | L | 0 - 1 |
| Sat 12 Mar 1966 | Birmingham City H | L | 0 - 1 |
| Sat 19 Mar 1966 | Leyton Orient A | D | 0 - 0 |
| Fri 25 Mar 1966 | Middlesbrough H | W | 4 - 1 |
| Sat 2 Apr 1966 | Bristol City A | L | 0 - 1 |
| Wed 6 Apr 1966 | Huddersfield Town H | W | 2 - 1 |
| Sat 9 Apr 1966 | Coventry City H | W | 2 - 0 |
| Mon 11 Apr 1966 | Huddersfield Town A | L | 0 - 2 |
| Sat 16 Apr 1966 | Rotherham United A | D | 3 - 3 |
| Sat 23 Apr 1966 | Wolverhampton Wanderers H | W | 2 - 0 |
| Sat 30 Apr 1966 | Norwich City A | W | 3 - 1 |
| Sat 7 May 1966 | Bury H | W | 4 - 0 |
