3. Round | 10/12/1999 | Walsall FC | - | Gillingham FC | 1:1 | ||||
3. Round | 07/01/2000 | Gillingham FC | - | Walsall FC | 2:1 aet | ||||
4. Round | 10/01/2000 | Gillingham FC | - | Bradford City | 3:1 | ||||
Round of 16 | 28/01/2000 | Gillingham FC | - | Sheffield Wednesday | 3:1 | ||||
Quarter-finals | 19/02/2000 | Chelsea FC | - | Gillingham FC | 5:0 |