| Monday 26th September 1960 | |||
| Bristol Rovers | 2-1 | Fulham | |
| West Ham United | 3-1 | Charlton Athletic | |
| Monday 3rd October 1960 | |||
| Middlesbrough | 3-4 | Cardiff City | |
| Monday 10th October 1960 | |||
| Colchester United | 4-1 | Newcastle United | |
| Coventry City | 4-2 | Barrow | |
| Hull City | 0-0 | Bolton Wanderers | |
| Millwall | 1-7 | Chelsea | |
| Newport County | 2-2 | Southampton | |
| Rochdale | 1-1 | Scunthorpe United | |
| Stockport County | 2-0 | Carlisle United | |
| York City | 1-3 | Blackburn Rovers | |
| Tuesday 11th October 1960 | |||
| Ipswich Town | 0-2 | Barnsley | |
| Oldham Athletic | 2-1 | Hartlepool United | |
| Preston North End | 4-1 | Peterborough United | |
| Watford | 2-5 | Derby County | |
| Wednesday 12th October 1960 | |||
| Chester City | 2-2 | Leyton Orient | |
| Darlington | 2-0 | Crystal Palace | |
| Everton | 3-1 | Accrington St (old) | |
| Leicester City | 4-0 | Mansfield Town | |
| Lincoln City | 2-2 | Bradford Park Avenue | |
| Plymouth Argyle | 2-0 | Southport | |
| Monday 17th October 1960 | |||
| Queens Park Rangers | 2-2 | Port Vale | |
| Replay | |||
| Leyton Orient | 1-0 | Chester City | |
| Southampton | 2-2 | Newport County | aet |
| Wednesday 19th October 1960 | |||
| Exeter City | 1-1 | Manchester United | |
| Replay | |||
| Bolton Wanderers | 5-1 | Hull City | |
| Bradford Park Avenue | 1-0 | Lincoln City | |
| Port Vale | 3-1 | Queens Park Rangers | aet |
| Thursday 20th October 1960 | |||
| Replay | |||
| Scunthorpe United | 0-1 | Rochdale | |
| Wednesday 26th October 1960 | |||
| Replay | |||
| Manchester United | 4-1 | Exeter City | |
| 2nd Replay | |||
| Southampton | 5-3 | Newport County | |
