1. Round | 09/08/1999 | Carlisle United | - | Grimsby Town | 0:0 | ||||
1. Round | 23/08/1999 | Grimsby Town | - | Carlisle United | 6:0 | ||||
2. Round | 13/09/1999 | Grimsby Town | - | Leyton Orient | 4:1 | ||||
2. Round | 20/09/1999 | Leyton Orient | - | Grimsby Town | 1:0 | ||||
3. Round | 12/10/1999 | Leicester City | - | Grimsby Town | 2:0 |