| Final played at Crystal Palace, London | | date | Winner | score | Finalist | HT | att. | | Sat 15.04.99 | Sheffield United | 4-1 | Derby County | | |
| date | team 1 | score | team 2 | HT | | Sat 18.03.99 | Derby County | 3-1 | Stoke City | | | | Sat 18.03.99 | Sheffield United | 2-2 | Liverpool | | | | Thu 23.03.99 | Liverpool | 4-4 | Sheffield United | | | | Thu 30.03.99 | Sheffield United | 1-0 | Liverpool | | |
| date | team 1 | score | team 2 | HT | | Sat 25.02.99 | Nottingham Forest | 0-1 | Sheffield United | | | | Sat 25.02.99 | Southampton | 1-2 | Derby County | | | | Sat 25.02.99 | Stoke City | 4-1 | Tottenham Hotspur | | | | Sat 25.02.99 | West Bromwich Albion | 0-2 | Liverpool | | |
| date | Home | score | Away | HT | | Sat 11.02.99 | Derby County | 2-1 | Wolverhampton Wanderers | | | | Sat 11.02.99 | Everton | 0-1 | Nottingham Forest | | | | Sat 11.02.99 | Liverpool | 3-1 | Newcastle United | | | | Sat 11.02.99 | Notts County | 0-1 | Southampton | | | | Sat 11.02.99 | Preston North End | 2-2 | Sheffield United | | | | Thu 16.02.99 | Sheffield United | 2-1 | Preston North End | | r | | Sat 11.02.99 | Stoke City | 2-2 | Small Heath | | | | Wed 15.02.99 | Small Heath | 1-2 | Stoke City | | r | | Sat 11.02.99 | Tottenham Hotspur | 2-1 | Sunderland AFC | | | | Sat 11.02.99 | West Bromwich Albion | 2-1 | Bury | | |
| date | Home | score | Away | HT | | Sat 28.01.99 | Bristol City | 2-4 | Sunderland AFC | | | | Sat 28.01.99 | Burnley | 2-2 | Sheffield United | | | | Thu 02.02.99 | Sheffield United | 2-1 | Burnley | | r | | Sat 28.01.99 | Everton | 3-1 | Jarrow | | | | Sat 28.01.99 | Glossop | 0-1 | Newcastle United | | | | Sat 28.01.99 | Heanor Town | 0-3 | Bury | | | | Sat 28.01.99 | Liverpool | 2-0 | Blackburn Rovers | | | | Sat 28.01.99 | New Brompton | 0-1 | Southampton | | | | Sat 28.01.99 | Nottingham Forest | 2-1 | Aston Villa | | | | Sat 28.01.99 | Notts County | 2-0 | Kettering Town | | | | Sat 28.01.99 | Preston North End | 7-0 | Grimsby Town | | | | Sat 28.01.99 | The Wednesday | 2-2 | Stoke City | | | | Thu 02.02.99 | Stoke City | 2-0 | The Wednesday | | r | | Sat 28.01.99 | Small Heath | 3-2 | Manchester City | | | | Sat 28.01.99 | Tottenham Hotspur | 1-1 | Newton Heath | | | | Wed 01.02.99 | Newton Heath | 3-5 | Tottenham Hotspur | | r | | Sat 28.01.99 | West Bromwich Albion | 8-0 | South Shore | | | | Sat 28.01.99 | Wolverhampton Wanderers | 0-0 | Bolton Wanderers | 0-0 | | | Wed 01.02.99 | Bolton Wanderers | 0-1 | Wolverhampton Wanderers | | r | | Sat 28.01.99 | Woolwich Arsenal | 0-6 | Derby County | | |
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