| 1. Round | 09/08/1999 | Hartlepool United | - | Crewe Alexandra | 3:3 | ||||
| 1. Round | 23/08/1999 | Crewe Alexandra | - | Hartlepool United | 1:0 |
| 1. Round | 09/08/1999 | Hartlepool United | - | Crewe Alexandra | 3:3 | ||||
| 1. Round | 23/08/1999 | Crewe Alexandra | - | Hartlepool United | 1:0 |
| Christopher Freestone | |
| Born: | 04.09.1971 |
| Place of birth: |
Nottingham, 
England |
| Nationality: |
England
|
| Height: | 180 cm |
| Weight: | 73 kg |