1. Round | 12/08/2000 | Gillingham FC | - | Stockport County | 1:3 | ||||
2. Round | 19/08/2000 | Tranmere Rovers | - | Gillingham FC | 3:2 | ||||
3. Round | 25/08/2000 | Gillingham FC | - | Portsmouth FC | 1:1 | ||||
4. Round | 28/08/2000 | Burnley FC | - | Gillingham FC | 1:1 | ||||
5. Round | 02/09/2000 | Gillingham FC | - | Wolverhampton Wanderers | 1:0 | ||||
6. Round | 09/09/2000 | Grimsby Town | - | Gillingham FC | 1:0 | ||||
7. Round | 13/09/2000 | Queens Park Rangers | - | Gillingham FC | 2:2 | ||||
8. Round | 16/09/2000 | Gillingham FC | - | Huddersfield Town | 2:1 | ||||
9. Round | 23/09/2000 | Fulham FC | - | Gillingham FC | 3:0 | ||||
10. Round | 30/09/2000 | Gillingham FC | - | Sheffield Wednesday | 2:0 | ||||
11. Round | 06/10/2000 | Gillingham FC | - | Bolton Wanderers | 2:2 | ||||
12. Round | 14/10/2000 | Wimbledon FC | - | Gillingham FC | 4:4 |