| Date | Opponents | Comp | Res | Venue |
|---|---|---|---|---|
| Sat 22 Aug 1959 | Middlesbrough | League | D 0-0 | Ayresome Park |
| Wed 26 Aug 1959 | Lincoln City | League | W 2-0 | Sincil Bank |
| Sat 29 Aug 1959 | STOKE CITY | League | D 2-2 | Fratton Park |
| Wed 02 Sep 1959 | LINCOLN CITY | League | L 1-2 | Fratton Park |
| Sat 05 Sep 1959 | Brighton & Hove Albion | League | L 1-3 | Goldstone Ground |
| Wed 09 Sep 1959 | ASTON VILLA | League | L 1-2 | Fratton Park |
| Sat 12 Sep 1959 | SWANSEA TOWN | League | L 1-3 | Fratton Park |
| Mon 14 Sep 1959 | Aston Villa | League | L 2-5 | Villa Park |
| Sat 19 Sep 1959 | Bristol Rovers | League | L 0-2 | Eastville Stadium |
| Sat 26 Sep 1959 | IPSWICH TOWN | League | L 0-2 | Fratton Park |
| Sat 03 Oct 1959 | Huddersfield Town | League | L 3-6 | Leeds Road |
| Sat 10 Oct 1959 | Derby County | League | L 0-1 | Baseball Ground |
| Sat 17 Oct 1959 | PLYMOUTH ARGYLE | League | W 1-0 | Fratton Park |
| Sat 24 Oct 1959 | Liverpool | League | D 1-1 | Anfield |
| Sat 31 Oct 1959 | CHARLTON ATHLETIC | League | D 2-2 | Fratton Park |
| Sat 07 Nov 1959 | Bristol City | League | L 0-2 | Ashton Gate |
| Sat 14 Nov 1959 | SCUNTHORPE UNITED | League | W 4-0 | Fratton Park |
| Sat 21 Nov 1959 | Rotherham United | League | L 1-2 | Millmoor |
| Sat 28 Nov 1959 | CARDIFF CITY | League | D 1-1 | Fratton Park |
| Sat 05 Dec 1959 | Hull City | League | W 3-1 | Boothferry Park |
| Sat 12 Dec 1959 | SHEFFIELD UNITED | League | L 0-2 | Fratton Park |
| Sat 19 Dec 1959 | MIDDLESBROUGH | League | W 6-3 | Fratton Park |
| Sat 26 Dec 1959 | Leyton Orient | League | W 2-1 | Brisbane Road |
| Mon 28 Dec 1959 | LEYTON ORIENT | League | D 1-1 | Fratton Park |
| Sat 02 Jan 1960 | Stoke City | League | L 0-4 | Victoria Ground |
| Sat 16 Jan 1960 | BRIGHTON & HOVE ALBION | League | D 2-2 | Fratton Park |
| Sat 23 Jan 1960 | Swansea Town | League | D 1-1 | Vetch Field |
| Sat 06 Feb 1960 | BRISTOL ROVERS | League | L 4-5 | Fratton Park |
| Sat 13 Feb 1960 | Ipswich Town | League | D 1-1 | Portman Road |
| Sat 20 Feb 1960 | HUDDERSFIELD TOWN | League | L 0-2 | Fratton Park |
| Sat 27 Feb 1960 | DERBY COUNTY | League | L 2-3 | Fratton Park |
| Sat 05 Mar 1960 | Plymouth Argyle | League | D 1-1 | Home Park |
| Sat 12 Mar 1960 | LIVERPOOL | League | W 2-1 | Fratton Park |
| Sat 19 Mar 1960 | Cardiff City | League | W 4-1 | Ninian Park |
| Sat 26 Mar 1960 | BRISTOL CITY | League | W 2-0 | Fratton Park |
| Sat 02 Apr 1960 | Scunthorpe United | League | L 0-1 | Old Showground |
| Sat 09 Apr 1960 | ROTHERHAM UNITED | League | W 2-0 | Fratton Park |
| Fri 15 Apr 1960 | Sunderland | League | L 0-2 | Roker Park |
| Sat 16 Apr 1960 | Sheffield United | League | D 0-0 | Bramall Lane |
| Mon 18 Apr 1960 | SUNDERLAND | League | L 1-2 | Fratton Park |
| Sat 23 Apr 1960 | HULL CITY | League | D 1-1 | Fratton Park |
| Sat 30 Apr 1960 | Charlton Athletic | League | L 1-6 | The Valley |