| Monday 27th August 1990 | |||
| 1st Leg | |||
| Stockport County | 0-2 | Burnley | |
| Tuesday 28th August 1990 | |||
| 1st Leg | |||
| Birmingham City | 0-1 | Bournemouth | |
| Brentford | 2-0 | Hereford United | |
| Carlisle United | 1-0 | Scunthorpe United | |
| Chesterfield | 1-2 | Hartlepool United | |
| Darlington | 0-0 | Blackpool | |
| Doncaster Rovers | 2-6 | Rotherham United | |
| Fulham | 1-2 | Peterborough United | |
| Gillingham | 1-0 | Shrewsbury Town | |
| Grimsby Town | 2-1 | Crewe Alexandra | |
| Halifax Town | 2-0 | Lincoln City | |
| Mansfield Town | 1-1 | Cardiff City | |
| Middlesbrough | 1-1 | Tranmere Rovers | |
| Preston North End | 2-0 | Chester City | |
| Reading | 0-1 | Oxford United | |
| Rochdale | 4-0 | Scarborough | |
| Southend United | 2-1 | Aldershot | |
| Walsall | 4-2 | Cambridge United | |
| Wigan Athletic | 0-1 | Barnsley | |
| York City | 0-1 | Wrexham | |
| Wednesday 29th August 1990 | |||
| 1st Leg | |||
| Bradford City | 2-0 | Bury | |
| Brighton and Hove A | 0-2 | Northampton Town | |
| Bristol Rovers | 1-2 | Torquay United | |
| Exeter City | 1-1 | Notts County | |
| Huddersfield Town | 0-3 | Bolton Wanderers | |
| Maidstone Utd (old) | 2-2 | Leyton Orient | |
| Stoke City | 0-0 | Swansea City | |
| West Bromwich Albion | 2-2 | Bristol City | |
| Monday 3rd September 1990 | |||
| 2nd Leg | |||
| Tranmere Rovers | 1-2 | Middlesbrough | (2-3) |
| Tuesday 4th September 1990 | |||
| 2nd Leg | |||
| Aldershot | 2-2 | Southend United | (3-4) |
| Barnsley | 0-1 | Wigan Athletic | aet (1-1) |
| (Barnsley won on penalties) | |||
| Blackpool | 1-1 | Darlington | aet (1-1) |
| (Darlington won on away goals) | |||
| Bolton Wanderers | 2-1 | Huddersfield Town | (5-1) |
| Bournemouth | 1-1 | Birmingham City | (2-1) |
| Burnley | 0-1 | Stockport County | (2-1) |
| Bury | 3-2 | Bradford City | aet (3-4) |
| Cambridge United | 2-1 | Walsall | (4-5) |
| Cardiff City | 3-0 | Mansfield Town | (4-1) |
| Chester City | 5-1 | Preston North End | aet (5-3) |
| Crewe Alexandra | 1-0 | Grimsby Town | aet (2-2) |
| (Crewe Alexandra won on away goals) | |||
| Leyton Orient | 4-1 | Maidstone Utd (old) | (6-3) |
| Northampton Town | 1-1 | Brighton and Hove A | (3-1) |
| Notts County | 1-0 | Exeter City | (2-1) |
| Peterborough United | 2-0 | Fulham | (4-1) |
| Rotherham United | 2-1 | Doncaster Rovers | (8-3) |
| Scunthorpe United | 1-1 | Carlisle United | (1-2) |
| Shrewsbury Town | 2-0 | Gillingham | (2-1) |
| Swansea City | 0-1 | Stoke City | (0-1) |
| Torquay United | 1-1 | Bristol Rovers | (3-2) |
| Wrexham | 2-0 | York City | (3-0) |
| Wednesday 5th September 1990 | |||
| 2nd Leg | |||
| Bristol City | 1-0 | West Bromwich Albion | aet (3-2) |
| Hereford United | 1-0 | Brentford | (1-2) |
| Lincoln City | 1-0 | Halifax Town | (1-2) |
| Oxford United | 2-1 | Reading | (3-1) |
| Scarborough | 3-3 | Rochdale | (3-7) |
| Tuesday 11th September 1990 | |||
| 2nd Leg | |||
| Hartlepool United | 2-2 | Chesterfield | (4-3) |
