| Friday 5th December 1986 | |||
| Southend United | 4-4 | Northampton Town | |
| Saturday 6th December 1986 | |||
| Aldershot | 3-2 | Colchester United | |
| Bolton Wanderers | 2-0 | Tranmere Rovers | |
| Bournemouth | 0-1 | Leyton Orient | |
| Bristol City | 1-1 | Bath City | |
| Caernarfon Town | 0-0 | York City | |
| Chester City | 3-1 | Doncaster Rovers | |
| Chorley | 0-0 | Preston North End | (n) |
| Darlington | 0-5 | Wigan Athletic | |
| Fulham | 2-0 | Newport County | |
| Gillingham | 2-0 | Chelmsford City | |
| Rochdale | 1-4 | Wrexham | |
| Scunthorpe United | 1-0 | Runcorn Halton | |
| Swansea City | 3-0 | Slough Town | |
| Swindon Town | 3-0 | Enfield | |
| Telford United | 1-0 | Altrincham | |
| Walsall | 5-0 | Port Vale | |
| Sunday 7th December 1986 | |||
| Maidstone Utd (old) | 1-0 | Cambridge United | |
| Notts County | 0-1 | Middlesbrough | |
| Tuesday 9th December 1986 | |||
| Cardiff City | 2-0 | Brentford | |
| Replay | |||
| Bristol City | 3-0 | Bath City | |
| Preston North End | 5-0 | Chorley | |
| York City | 1-2 | Caernarfon Town | |
| Wednesday 10th December 1986 | |||
| Replay | |||
| Northampton Town | 3-2 | Southend United | |
