| 3. Round | 05/01/1990 | Cambridge United | - | Darlington FC | 0:0 | ||||
| 3. Round | 08/01/1990 | Darlington FC | - | Cambridge United | 1:3 | ||||
| 4. Round | 26/01/1990 | Millwall FC | - | Cambridge United | 1:1 | ||||
| 4. Round | 30/01/1990 | Cambridge United | - | Millwall FC | 1:0 aet | ||||
| Round of 16 | 16/02/1990 | Bristol City | - | Cambridge United | 0:0 | ||||
| Round of 16 | 20/02/1990 | Cambridge United | - | Bristol City | 1:1 aet | ||||
| Round of 16 | 26/02/1990 | Cambridge United | - | Bristol City | 5:1 | ||||
| Quarter-finals | 09/03/1990 | Cambridge United | - | Crystal Palace | 0:1 |
England