| 3. Round | 10/12/1999 | Hull City | - | Chelsea FC | 1:6 | ||||
| 4. Round | 18/01/2000 | Chelsea FC | - | Nottingham Forest | 2:0 | ||||
| Round of 16 | 30/01/2000 | Chelsea FC | - | Leicester City | 2:1 | ||||
| Quarter-finals | 20/02/2000 | Chelsea FC | - | Gillingham FC | 5:0 |  |
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| Semi-finals | 09/04/2000 | Newcastle United | - | Chelsea FC | 1:2 | ||||
| Final | 20/05/2000 | Aston Villa | - | Chelsea FC | 0:1 |
Norway