| September 13, 1958 |
Swansea Town vs. Sunderland |
Vetch Field |
Second Division |
| September 27, 1958 |
West Bromwich Albion vs. Everton |
The Hawthorns |
First Division |
| October 4, 1958 |
Rotherham United vs. Brighton & Hove Albion |
Millmoor |
First Division |
| November 22, 1958 |
Chelsea vs. Arsenal |
Stamford Bridge |
First Division |
| November 29, 1958 |
Everton vs. Chelsea |
Goodison Park |
First Division |
| November 29, 1958 |
West Bromwich Albion vs. Tottenham Hotspur |
The Hawthorns |
First Division |
| December 20, 1958 |
Crewe Alexandra vs. Crystal Palace |
Gresty Road |
Fourth Division |
| December 26, 1958 |
Derby County vs. Swansea Town |
Baseball Ground |
Second Division |
| January 3, 1959 |
Fulham vs. Swansea Town |
Craven Cottage |
Second Division |
| January 31, 1959 |
Manchester United vs. Newcastle United |
Old Trafford |
First Division |
| March 14, 1959 |
Manchester City vs. Newcastle United |
Maine Road |
First Division |
| March 14, 1959 |
Swansea Town vs. Huddersfield Town |
Vetch Field |
Second Division |
| March 18, 1959 |
Norwich City vs. Luton Town |
St. Andrew's |
FA Cup |
| March 21, 1959 |
Nottingham Forest vs. Burnley |
City Ground |
First Division |
| March 30, 1959 |
Aston Villa vs. Tottenham Hotspur |
Villa Park |
First Division |
| March 31, 1959 |
Sheffield United vs. Brighton & Hove Albion |
Bramall Lane |
Second Division |
| March 31, 1959 |
West Bromwich Albion vs. Manchester City |
The Hawthorns |
First Division |
| April 4, 1959 |
Aston Villa vs. Leicester City |
Villa Park |
First Division |
| April 11, 1959 |
Arsenal vs. Chelsea |
Arsenal Stadium |
First Division |
| April 27, 1959 |
Crystal Palace vs. Arsenal |
Selhurst Park |
Southern Floodlight Challenge Cup |
