Semifinals1st leg – May 16; 2nd leg – May 19/20, 1999
Agg 0–2Legs +Legs −
- 1st legBirmingham 0–1 Watford
- 2nd legWatford 1–0 Birmingham
- 1st legBirmingham 0–1 Watford
- 2nd legWatford 1–0 Birmingham
Agg 0–2Agg 3–5Legs +Legs −
- 1st legIpswich 0–1 Bolton
- 2nd legBolton 4–3 Ipswich
- 1st legIpswich 0–1 Bolton
- 2nd legBolton 4–3 Ipswich
Agg 3–5
Final at Wembley May 31, 1999
Sources: Wikipedia, API-Football