| 3. Round | 03/01/1999 | Preston North End | - | Arsenal FC | 2:4 |  |
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| 4. Round | 23/01/1999 | Wolverhampton Wanderers | - | Arsenal FC | 1:2 | |
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| Round of 16 | 22/02/1999 | Arsenal FC | - | Sheffield United | 2:1 | |
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| Quarter-finals | 05/03/1999 | Arsenal FC | - | Derby County | 1:0 | ||||
| Semi-finals | 10/04/1999 | Manchester United | - | Arsenal FC | 0:0 aet | ||||
| Semi-finals | 13/04/1999 | Arsenal FC | - | Manchester United | 1:2 aet |
Netherlands
