| Sunday 16th November 1986 | |||
| Darlington | 2-1 | Mansfield Town | |
| Northampton Town | 3-0 | Peterborough United | |
| Monday 17th November 1986 | |||
| Replay | |||
| Chelmsford City | 2-1 | Woking | |
| Tuesday 18th November 1986 | |||
| Replay | |||
| Altrincham | 4-0 | Frickley Athletic | |
| Bognor Regis Town | 0-1 | Slough Town | |
| Bolton Wanderers | 1-1 | Halifax Town | aet |
| Carlisle United | 0-3 | Notts County | |
| Colchester United | 2-0 | Bishop's Stortford | |
| Doncaster Rovers | 3-2 | Whitby Town | |
| Enfield | 3-0 | Dartford | |
| Rotherham United | 1-1 | Chester City | aet |
| Wolverhampton Wndrs | 1-1 | Chorley | aet |
| Wednesday 19th November 1986 | |||
| Replay | |||
| Boston United | 1-2 | Runcorn Halton | aet |
| Cambridge United | 2-0 | Exeter City | |
| Monday 24th November 1986 | |||
| Replay | |||
| Fulham | 4-0 | Hereford United | |
| Maidstone Utd (old) | 4-1 | Welling United | |
| Swansea City | 4-1 | Wealdstone | |
| 2nd Replay | |||
| Chester City | 1-0 | Rotherham United | |
| Chorley | 3-0 | Wolverhampton Wndrs | (n) |
| Halifax Town | 1-3 | Bolton Wanderers | |
| Wednesday 3rd December 1986 | |||
| Bristol Rovers | 0-0 | Brentford | |
| Saturday 6th December 1986 | |||
| Replay | |||
| Brentford | 2-0 | Bristol Rovers | |
