| 3. Runde | 06.01.1990 | Middlesbrough FC | - | Everton FC | 0:0 | ||||
| 3. Runde | 10.01.1990 | Everton FC | - | Middlesbrough FC | 1:1 n.V. | ||||
| 3. Runde | 17.01.1990 | Everton FC | - | Middlesbrough FC | 1:0 | ||||
| 4. Runde | 28.01.1990 | Sheffield Wednesday | - | Everton FC | 1:2 | ||||
| Achtelfinale | 17.02.1990 | Oldham Athletic | - | Everton FC | 2:2 |  |
 |
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| Achtelfinale | 21.02.1990 | Everton FC | - | Oldham Athletic | 1:1 n.V. | |
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| Achtelfinale | 10.03.1990 | Oldham Athletic | - | Everton FC | 2:1 n.V. |
Schottland