| Fulham FC v Gillingham FC 13/04/1999 | £3.50 | |
| Brighton & Hove Albion FC v Shrewsbury Town FC 13/04/1999 | £6.50 | |
| Middlesbrough FC v Chelsea FC 14/04/1999 | £3.50 | |
| Manchester City FC v Luton Town FC 14/04/1999 | £6.00 | |
| West Ham United FC v Derby County FC 17/04/1999 | £5.00 | |
| Nottingham Forest FC v Tottenham Hotspur FC 17/04/1999 | £4.50 | |
| Halifax Town A.F.C v Brighton & Hove Albion FC 17/04/1999 | £6.00 | |
| Luton Town FC v Lincoln City FC 17/04/1999 | £4.00 | |
| Grimsby Town FC v Bury FC 17/04/1999 | £6.00 | |
| Charlton Athletic FC v Leeds United FC 17/04/1999 | £3.00 | |
| Southampton FC v Blackburn Rovers FC 17/04/1999 | £2.50 | |
| Southampton FC v Blackburn Rovers FC 17/04/1999 | £2.00 |