Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 24.08.1999 |  | 1. Round 2nd leg | Hull City - Rotherham Utd | HUL - ROT | 2:0 | 4.373 |
| 14.09.1999 | | 2. Round First leg | Hull City - Liverpool | HUL - LIV | 1:5 | 10.034 |
Boothferry Park
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 24.08.1999 | | 1. Round 2nd leg | Hull City - Rotherham Utd | HUL - ROT | 2:0 | 4.373 |
| 14.09.1999 | | 2. Round First leg | Hull City - Liverpool | HUL - LIV | 1:5 | 10.034 |