| Date | Opponents | Comp | Res | Venue |
|---|---|---|---|---|
| Sat 23 Aug 1958 | WEST HAM UNITED | League | L 1-2 | Fratton Park |
| Mon 25 Aug 1958 | Aston Villa | League | L 2-3 | Villa Park |
| Sat 30 Aug 1958 | Nottingham Forest | League | L 0-5 | City Ground |
| Wed 03 Sep 1958 | ASTON VILLA | League | W 5-2 | Fratton Park |
| Sat 06 Sep 1958 | CHELSEA | League | D 2-2 | Fratton Park |
| Wed 10 Sep 1958 | West Bromwich Albion | League | W 2-1 | The Hawthorns |
| Sat 13 Sep 1958 | Blackpool | League | D 1-1 | Bloomfield Road |
| Wed 17 Sep 1958 | WEST BROMWICH ALBION | League | L 2-6 | Fratton Park |
| Sat 20 Sep 1958 | BLACKBURN ROVERS | League | W 2-1 | Fratton Park |
| Sat 27 Sep 1958 | Newcastle United | League | L 0-2 | St. James Park |
| Sat 04 Oct 1958 | TOTTENHAM HOTSPUR | League | D 1-1 | Fratton Park |
| Sat 11 Oct 1958 | LEEDS UNITED | League | W 2-0 | Fratton Park |
| Sat 18 Oct 1958 | Manchester City | League | L 2-3 | Maine Road |
| Sat 25 Oct 1958 | LUTON TOWN | League | D 2-2 | Fratton Park |
| Sat 01 Nov 1958 | Birmingham City | League | D 2-2 | St. Andrews |
| Sat 08 Nov 1958 | LEICESTER CITY | League | W 4-1 | Fratton Park |
| Sat 15 Nov 1958 | Preston North End | League | L 1-3 | Deepdale |
| Sat 22 Nov 1958 | BURNLEY | League | W 4-2 | Fratton Park |
| Sat 29 Nov 1958 | Bolton Wanderers | League | L 1-2 | Burnden Park |
| Sat 06 Dec 1958 | ARSENAL | League | L 0-1 | Fratton Park |
| Sat 13 Dec 1958 | Everton | League | L 1-2 | Goodison Park |
| Sat 20 Dec 1958 | West Ham United | League | L 0-6 | Boleyn Ground |
| Fri 26 Dec 1958 | WOLVERHAMPTON WANDERERS | League | L 3-5 | Fratton Park |
| Sat 27 Dec 1958 | Wolverhampton Wanderers | League | L 0-7 | Molineux |
| Sat 03 Jan 1959 | NOTTINGHAM FOREST | League | L 0-1 | Fratton Park |
| Sat 17 Jan 1959 | Chelsea | League | D 2-2 | Stamford Bridge |
| Sat 31 Jan 1959 | BLACKPOOL | League | L 1-2 | Fratton Park |
| Sat 07 Feb 1959 | Blackburn Rovers | League | L 1-2 | Ewood Park |
| Sat 21 Feb 1959 | Tottenham Hotspur | League | D 4-4 | White Hart Lane |
| Sat 28 Feb 1959 | Leeds United | League | D 1-1 | Elland Road |
| Sat 07 Mar 1959 | MANCHESTER CITY | League | L 3-4 | Fratton Park |
| Wed 11 Mar 1959 | NEWCASTLE UNITED | League | L 1-5 | Fratton Park |
| Sat 21 Mar 1959 | BIRMINGHAM CITY | League | D 1-1 | Fratton Park |
| Fri 27 Mar 1959 | Manchester United | League | L 1-6 | Old Trafford |
| Sat 28 Mar 1959 | Leicester City | League | L 1-3 | Filbert Street |
| Mon 30 Mar 1959 | MANCHESTER UNITED | League | L 1-3 | Fratton Park |
| Sat 04 Apr 1959 | PRESTON NORTH END | League | L 1-2 | Fratton Park |
| Sat 11 Apr 1959 | Burnley | League | L 1-2 | Turf Moor |
| Wed 15 Apr 1959 | EVERTON | League | L 2-3 | Fratton Park |
| Sat 18 Apr 1959 | BOLTON WANDERERS | League | L 0-1 | Fratton Park |
| Wed 22 Apr 1959 | Luton Town | League | L 1-3 | Kenilworth Road |
| Sat 25 Apr 1959 | Arsenal | League | L 2-5 | Highbury |