| 2. Round | 21/09/1987 | Carlisle United | - | Oldham Athletic | 4:3 |  |
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| 2. Round | 06/10/1987 | Oldham Athletic | - | Carlisle United | 4:1 aet | ||||
| 3. Round | 27/10/1987 | Leeds United | - | Oldham Athletic | 2:2 | ||||
| 3. Round | 03/11/1987 | Oldham Athletic | - | Leeds United | 4:2 aet | ||||
| Round of 16 | 17/11/1987 | Everton FC | - | Oldham Athletic | 2:1 |
England