Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 02.01.1999 |  | 3. Round | Oldham Athletic - Chelsea | OLD - CHE | 0:2 | 12.770 |
| 24.08.1999 |  | 1. Round 2nd leg | Oldham Athletic - Stockport County | OLD - STO | 1:1 | 2.750 |
| 20.11.1999 | | 2. Round | Oldham Athletic - Swansea | OLD - SWA | 1:0 | 4.332 |