| 23-Aug-58 | Bristol Rovers | Home | League | 1-3 | Julians | 17364 | |
| 27-Aug-58 | Ipswich Town | Away | League | 1-2 | Elwood | 16869 | |
| 30-Aug-58 | Derby County | Away | League | 2-1 | McClellan, Julians | 22632 | |
| 4-Sep-58 | Ipswich Town | Home | League | 2-0 | McClellan, White | 11786 | |
| 6-Sep-58 | Barnsley | Home | League | 5-1 | Woosnam (3), Julians (2) | 13288 | |
| 11-Sep-58 | Swansea Town | Away | League | 3-3 | Hasty (2), McKnight | 20000 | |
| 13-Sep-58 | Scunthorpe United | Home | League | 2-1 | Julians, Lazarus | 15955 | |
| 18-Sep-58 | Swansea Town | Home | League | 0-0 | | 12938 | |
| 20-Sep-58 | Sheffield Wednesday | Away | League | 0-2 | | 28433 | |
| 27-Sep-58 | Fulham | Home | League | 0-2 | | 24681 | |
| 4-Oct-58 | Lincoln City | Away | League | 0-2 | | 9777 | |
| 11-Oct-58 | Rotherham United | Away | League | 1-1 | Andrews | 6730 | |
| 18-Oct-58 | Sheffield United | Home | League | 1-1 | Andrews | 13562 | |
| 25-Oct-58 | Brighton & Hove Albion | Away | League | 2-2 | McClellan (2) | 26265 | |
| 1-Nov-58 | Huddersfield Town | Home | League | 2-5 | Facey (2) | 13928 | |
| 8-Nov-58 | Liverpool | Away | League | 0-3 | | 34920 | |
| 15-Nov-58 | Middlesbrough | Home | League | 5-2 | Julians (3), White, Lazarus | 10234 | |
| 22-Nov-58 | Charlton Athletic | Away | League | 1-4 | Lazarus | 15877 | |
| 29-Nov-58 | Bristol City | Home | League | 4-2 | Elwood (4) | 9591 | |
| 6-Dec-58 | Cardiff City | Away | League | 1-2 | Lewis | 15184 | |
| 13-Dec-58 | Grimsby Town | Home | League | 0-1 | | 7672 | |
| 20-Dec-58 | Bristol Rovers | Away | League | 3-1 | White, Lewis, Lazarus | 10004 | |
| 26-Dec-58 | Stoke City | Home | League | 0-1 | | 12173 | |
| 27-Dec-58 | Stoke City | Away | League | 2-3 | Burridge, White | 30070 | |
| 1-Jan-59 | Sunderland | Away | League | 0-4 | | 33040 | |
| 3-Jan-59 | Derby County | Home | League | 1-3 | Elwood | 11755 | |
| 10-Jan-59 | Blackburn Rovers | Away | FAC r3 | 2-4 | Lewis (2) | 27728 | |
| 31-Jan-59 | Scunthorpe United | Away | League | 0-2 | | 10295 | |
| 7-Feb-59 | Sheffield Wednesday | Home | League | 0-2 | | 11845 | |
| 14-Feb-59 | Fulham | Away | League | 2-5 | Baily, Andrews | 20478 | |
| 21-Feb-59 | Lincoln City | Home | League | 0-0 | | 10106 | |
| 28-Feb-59 | Liverpool | Home | League | 1-3 | Facey (pen) | 14064 | |
| 7-Mar-59 | Sheffield United | Away | League | 3-2 | Brown, Johnston (2) | 14769 | |
| 14-Mar-59 | Brighton & Hove Albion | Home | League | 2-2 | Brown, Johnston | 15811 | |
| 21-Mar-59 | Huddersfield Town | Away | League | 0-0 | | 10065 | |
| 28-Mar-59 | Rotherham United | Home | League | 2-0 | Baily, Brown | 11860 | |
| 30-Mar-59 | Sunderland | Home | League | 6-0 | Johnston, Brown (4), White | 15613 | |
| 4-Apr-59 | Middlesbrough | Away | League | 2-4 | Wright (pen), Elwood | 20432 | |
| 11-Apr-59 | Charlton Athletic | Home | League | 6-1 | Elwood (3), Facey (pen), Brown, Baily | 15280 | |
| 18-Apr-59 | Bristol City | Away | League | 1-0 | Johnston | 14444 | |
| 21-Apr-59 | Grimsby Town | Away | League | 1-4 | Johnston | 8000 | |
| 25-Apr-59 | Cardiff City | Home | League | 3-0 | Brown, Johnston (2) | 11465 | |
| 29-Apr-59 | Barnsley | Away | League | 3-1 | Johnston (2), Brown | 7780 | |
