| Date | Opponent | Score | Att. | ||||
|---|---|---|---|---|---|---|---|
| 16 August 1958 | Home | Blues v. Whites | Friendly | 5–1 | W | 0 | → |
| 23 August 1958 | Away | Bournemouth + BA | League | 4–1 | W | 14219 | → |
| 27 August 1958 | Home | Reading | League | 2–2 | D | 15479 | → |
| 30 August 1958 | Home | Norwich City | League | 1–0 | W | 15661 | → |
| 3 September 1958 | Away | Reading | League | 0–3 | L | 13605 | → |
| 6 September 1958 | Away | Chesterfield | League | 0–4 | L | 11057 | → |
| 10 September 1958 | Home | Tranmere Rovers | League | 1–3 | L | 11057 | → |
| 13 September 1958 | Away | Bury | League | 3–2 | W | 11505 | → |
| 15 September 1958 | Away | Tranmere Rovers | League | 1–1 | D | 12963 | → |
| 20 September 1958 | Home | Q P R | League | 4–0 | W | 13534 | → |
| 24 September 1958 | Home | Colchester United | League | 1–1 | D | 11471 | → |
| 27 September 1958 | Away | Rochdale | League | 1–1 | D | 5196 | → |
| 29 September 1958 | Away | Colchester United | League | 1–0 | W | 6833 | → |
| 4 October 1958 | Home | Doncaster Rovers | League | 5–0 | W | 11889 | → |
| 8 October 1958 | Away | Plymouth Argyle | League | 1–3 | L | 25349 | → |
| 11 October 1958 | Home | Halifax Town | League | 3–2 | W | 12307 | → |
| 17 October 1958 | Away | Accrington Stanley | League | 0–3 | L | 8113 | → |
| 20 October 1958 | Away | Stockport County | League | 1–0 | W | 11900 | → |
| 23 October 1958 | Away | Barking | Friendly | 0–0 | D | 0 | → |
| 25 October 1958 | Home | Southampton | League | 1–1 | D | 13289 | → |
| 29 October 1958 | Away | Bury Town | Friendly | 0–0 | D | 0 | → |
| 1 November 1958 | Away | Wrexham | League | 1–3 | L | 13172 | → |
| 8 November 1958 | Home | Bradford City | League | 1–1 | D | 14176 | → |
| 15 November 1958 | Home | Yeovil Town | FA Cup | 0–0 | D | 15265 | → |
| 20 November 1958 | Away | Yeovil Town | FA Cup | 0–1 | L | 11000 | → |
| 22 November 1958 | Home | Mansfield Town | League | 5–1 | W | 9337 | → |
| 29 November 1958 | Away | Swindon Town | League | 1–2 | L | 10000 | → |
| 6 December 1958 | Home | Gillingham | Friendly | 3–0 | W | 0 | → |
| 13 December 1958 | Away | Notts County | League | 4–1 | W | 7121 | → |
| 20 December 1958 | Home | Bournemouth + BA | League | 2–0 | W | 10082 | → |
| 27 December 1958 | Home | Stockport County | League | 3–1 | W | 15315 | → |
| 3 January 1959 | Away | Norwich City | League | 0–4 | L | 19077 | → |
| 10 January 1959 | Away | Hull City | League | 2–3 | L | 12908 | → |
| 17 January 1959 | Home | Chesterfield | League | 2–5 | L | 9895 | → |
| 24 January 1959 | Home | Plymouth Argyle | League | 0–0 | D | 12430 | → |
| 31 January 1959 | Home | Bury | League | 1–0 | W | 10885 | → |
| 7 February 1959 | Away | Q P R | League | 3–1 | W | 6099 | → |
| 14 February 1959 | Home | Rochdale | League | 3–1 | W | 8766 | → |
| 21 February 1959 | Away | Doncaster Rovers | League | 1–2 | L | 5727 | → |
| 28 February 1959 | Away | Halifax Town | League | 0–1 | L | 6861 | → |
| 7 March 1959 | Home | Accrington Stanley | League | 4–2 | W | 9343 | → |
| 14 March 1959 | Away | Southampton | League | 2–3 | L | 9251 | → |
| 21 March 1959 | Home | Wrexham | League | 4–1 | W | 8699 | → |
| 28 March 1959 | Away | Bradford City | League | 1–6 | L | 9783 | → |
| 30 March 1959 | Home | Newport County | League | 1–0 | W | 9672 | → |
| 4 April 1959 | Home | Hull City | League | 1–1 | D | 12231 | → |
| 8 April 1959 | Home | Brentford | League | 2–0 | W | 8824 | → |
| 11 April 1959 | Away | Mansfield Town | League | 4–1 | W | 7143 | → |
| 13 April 1959 | Away | Newport County | League | 1–3 | L | 5070 | → |
| 18 April 1959 | Home | Swindon Town | League | 0–2 | L | 7384 | → |
| 25 April 1959 | Away | Brentford | League | 1–6 | L | 11260 | → |
| 27 April 1959 | Home | Portsmouth | Friendly | 1–3 | L | 0 | → |
| 29 April 1959 | Home | Notts County | League | 5–2 | W | 5774 | → |
| 1 May 1959 | Away | Chelmsford City | Friendly | 0–0 | D | 0 | → |
| 1 May 1959 | Home | All Star XI | Friendly | 4–5 | L | 0 | → |