Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 04.01.1999 |  | 3. Round | Preston North E - Arsenal | PNE - ARS | 2:4 | 21.099 |
| 10.08.1999 |  | 1. Round First leg | Preston North E - Wrexham AFC | PNE - WRX | 1:0 | 4.930 |
| 21.09.1999 | | 2. Round 2nd leg | Preston North E - Sheffield Utd | PNE - SHE | 3:0 | 5.658 |
| 20.11.1999 | | 2. Round | Preston North E - Enfield FC| | PNE - | 0:0 | 11.566 |
| 11.12.1999 | | 3. Round | Preston North E - Oldham Athletic | PNE - OLD | 2:1 | 9.940 |