| 2. Round | 18/09/1989 | Oldham Athletic | - | Leeds United | 2:1 |  |
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| 2. Round | 03/10/1989 | Leeds United | - | Oldham Athletic | 1:2 | |
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| 3. Round | 25/10/1989 | Oldham Athletic | - | Scarborough FC | 7:0 | |
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| Round of 16 | 21/11/1989 | Oldham Athletic | - | Arsenal FC | 3:1 | |
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| Quarter-finals | 23/01/1990 | Southampton FC | - | Oldham Athletic | 2:2 | |
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| Quarter-finals | 30/01/1990 | Oldham Athletic | - | Southampton FC | 2:0 | |
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| Semi-finals | 13/02/1990 | Oldham Athletic | - | West Ham United | 6:0 | |
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| Final | 29/04/1990 | Nottingham Forest | - | Oldham Athletic | 1:0 |
England