31st May 1999
| Final | Watford | 2-0 | Bolton Wanderers |
20th May 1999
| Semi Final 2nd Leg | Birmingham City | 1-0 | Watford |
19th May 1999
| Semi Final 2nd Leg | Ipswich Town | 4-3 | Bolton Wanderers |
16th May 1999
| Semi Final 1st Leg | Watford | 1-0 | Birmingham City |
| Semi Final 1st Leg | Bolton Wanderers | 1-0 | Ipswich Town |