| 3. Runde | 03.01.2009 | Macclesfield Town | - | Everton FC | 0:1 | ||||
| 4. Runde | 25.01.2009 | Liverpool FC | - | Everton FC | 1:1 | ||||
| 4. Runde | 04.02.2009 | Everton FC | - | Liverpool FC | 1:0 n.V. |  |
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| Achtelfinale | 15.02.2009 | Everton FC | - | Aston Villa | 3:1 | |
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| Halbfinale | 19.04.2009 | Manchester United | - | Everton FC | 2:4 i.E. | ||||
| Finale | 30.05.2009 | Chelsea FC | - | Everton FC | 2:1 | |
England