| 1. Round | 09/08/1999 | Blackpool FC | - | Tranmere Rovers | 2:1 | ||||
| 1. Round | 23/08/1999 | Tranmere Rovers | - | Blackpool FC | 3:1 |  |
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| 2. Round | 13/09/1999 | Tranmere Rovers | - | Coventry City | 5:1 | |
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| 2. Round | 21/09/1999 | Coventry City | - | Tranmere Rovers | 3:1 | ||||
| 3. Round | 11/10/1999 | Tranmere Rovers | - | Oxford United | 2:0 | ||||
| Round of 16 | 29/11/1999 | Tranmere Rovers | - | Barnsley FC | 4:0 | ||||
| Quarter-finals | 13/12/1999 | Tranmere Rovers | - | Middlesbrough FC | 2:1 | |
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| Semi-finals | 11/01/2000 | Bolton Wanderers | - | Tranmere Rovers | 0:1 | ||||
| Semi-finals | 25/01/2000 | Tranmere Rovers | - | Bolton Wanderers | 3:0 | |
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| Final | 26/02/2000 | Leicester City | - | Tranmere Rovers | 2:1 | |
England