*Watford FC 1-1 Birmingham City
| 20.05.1999 | Birmingham City | 1-0/p.6-7 | Watford FC | |
| 16.05.1999 | Watford FC | 1-0 | Birmingham City | |
*Bolton Wanderers 4-4 Ipswich Town
| 19.05.1999 | Ipswich Town | 4-3 AET | Bolton Wanderers | |
| 16.05.1999 | Bolton Wanderers | 1-0 | Ipswich Town | |