In
| Player | Team | Date | Fee |
|---|---|---|---|
| Frank Wignall | Horwich RMI | 5 May 1958 | £1,850 |
| Alex Parker | Falkirk | 27 May 1958 | £18,000 |
| Eddie O'Hara | Falkirk | 27 May 1958 | £7,500 |
| Peter Harburn | Brighton & Hove Albion | 29 July 1958 | £6,500 |
| Bobby Collins | Celtic | 12 September 1958 | £23,550 |
| Bobby Laverick | Chelsea | 17 February 1959 | £5,000 |
| Total (initial fees only): | £62,400 | ||
Out
| Player | Team | Date | Fee |
|---|---|---|---|
| Bennett Steele | Chesterfield | May 1958 | £100 |
| William Haughey | Falkirk | 27 May 1958 | £1,500 |
| Bert Llewellyn | Crewe Alexandra | 25 June 1958 | £500 |
| Fred Leeder | Darlington | 7 July 1958 | £600 |
| Don Donovan | Grimsby Town | 8 August 1958 | £9,500 |
| Peter Harburn | Scunthorpe United | 5 January 1959 | £4,000 |
| Wally Fielding | Southport | 14 January 1959 | £1,000 |
| Graham Williams | Swansea Town | 5 February 1959 | £4,000 |
| George Kirby | Sheffield Wednesday | 13 March 1959 | £8,000 |
| Total (initial fees only): | £29,200 | ||
- Bennett Steele (Chesterfield) – Transfer completed around 14th May 1958.
- William Haughey (Falkirk) – £1,500 is the reported transfer fee.
- Wally Fielding (Southport) – Wally Fielding joined Southport as a player-manager.
| Income | £29,200 |
| Expenditure | £62,400 |
| Net Spend | +£33,200 |