1. Round | 09/08/1999 | Hartlepool United | - | Crewe Alexandra | 3:3 | ||||
1. Round | 23/08/1999 | Crewe Alexandra | - | Hartlepool United | 1:0 | ||||
2. Round | 13/09/1999 | Crewe Alexandra | - | Ipswich Town | 2:1 | ||||
2. Round | 20/09/1999 | Ipswich Town | - | Crewe Alexandra | 1:1 | ||||
3. Round | 12/10/1999 | Tottenham Hotspur | - | Crewe Alexandra | 3:1 |