| Monday 24th September 1990 | |||
| 1st Leg | |||
| Port Vale | 0-2 | Oxford United | |
| Tuesday 25th September 1990 | |||
| 1st Leg | |||
| Bournemouth | 0-0 | Millwall | |
| Cardiff City | 1-1 | Portsmouth | |
| Carlisle United | 1-1 | Derby County | |
| Chester City | 0-1 | Arsenal | |
| Crystal Palace | 8-0 | Southend United | |
| Darlington | 3-0 | Swindon Town | |
| Hull City | 0-0 | Wolverhampton Wndrs | |
| Liverpool | 5-1 | Crewe Alexandra | |
| Luton Town | 1-1 | Bradford City | |
| Middlesbrough | 2-0 | Newcastle United | |
| Northampton Town | 0-1 | Sheffield United | |
| Notts County | 1-0 | Oldham Athletic | |
| Plymouth Argyle | 1-0 | Wimbledon | |
| Rochdale | 0-5 | Southampton | |
| Rotherham United | 1-1 | Blackburn Rovers | |
| Shrewsbury Town | 1-1 | Ipswich Town | |
| Sunderland | 0-1 | Bristol City | |
| Wrexham | 0-5 | Everton | |
| Wednesday 26th September 1990 | |||
| 1st Leg | |||
| Aston Villa | 1-0 | Barnsley | |
| Charlton Athletic | 2-2 | Leyton Orient | |
| Coventry City | 4-2 | Bolton Wanderers | |
| Halifax Town | 1-3 | Manchester United | |
| Leicester City | 1-0 | Leeds United | |
| Norwich City | 2-0 | Watford | |
| Nottingham Forest | 4-1 | Burnley | |
| Queens Park Rangers | 3-1 | Peterborough United | |
| Sheffield Wednesday | 2-1 | Brentford | |
| Torquay United | 0-4 | Manchester City | |
| Tottenham Hotspur | 5-0 | Hartlepool United | |
| Walsall | 0-5 | Chelsea | |
| West Ham United | 3-0 | Stoke City | |
| Tuesday 9th October 1990 | |||
| 2nd Leg | |||
| Arsenal | 5-0 | Chester City | (6-0) |
| Barnsley | 0-1 | Aston Villa | (0-2) |
| Blackburn Rovers | 1-0 | Rotherham United | (2-1) |
| Bolton Wanderers | 2-3 | Coventry City | (4-7) |
| Brentford | 1-2 | Sheffield Wednesday | (2-4) |
| Bristol City | 1-6 | Sunderland | (2-6) |
| Crewe Alexandra | 1-4 | Liverpool | (2-9) |
| Everton | 6-0 | Wrexham | (11-0) |
| Hartlepool United | 1-2 | Tottenham Hotspur | (1-7) |
| Ipswich Town | 3-0 | Shrewsbury Town | (4-1) |
| Leyton Orient | 1-0 | Charlton Athletic | (3-2) |
| Peterborough United | 1-1 | Queens Park Rangers | (2-4) |
| Portsmouth | 3-1 | Cardiff City | aet (4-2) |
| Southampton | 3-0 | Rochdale | (8-0) |
| Southend United | 1-2 | Crystal Palace | (1-10) |
| Swindon Town | 4-0 | Darlington | (4-3) |
| Watford | 0-3 | Norwich City | (0-5) |
| Wolverhampton Wndrs | 1-1 | Hull City | aet (1-1) |
| (Hull City won on away goals) | |||
| Wednesday 10th October 1990 | |||
| 2nd Leg | |||
| Bradford City | 1-1 | Luton Town | aet (2-2) |
| (Bradford City won on penalties) | |||
| Burnley | 0-1 | Nottingham Forest | (1-5) |
| Chelsea | 4-1 | Walsall | (9-1) |
| Derby County | 1-0 | Carlisle United | (2-1) |
| Leeds United | 3-0 | Leicester City | (3-1) |
| Manchester City | 0-0 | Torquay United | (4-0) |
| Manchester United | 2-1 | Halifax Town | (5-2) |
| Millwall | 2-1 | Bournemouth | (2-1) |
| Newcastle United | 1-0 | Middlesbrough | (1-2) |
| Oldham Athletic | 5-2 | Notts County | aet (5-3) |
| Oxford United | 0-0 | Port Vale | (2-0) |
| Sheffield United | 2-1 | Northampton Town | (3-1) |
| Stoke City | 1-2 | West Ham United | (1-5) |
| Wimbledon | 0-2 | Plymouth Argyle | (0-3) |
