| Bury FC v Stockport County FC 02/01/1999 | £5.00 | |
| Oldham Athletic FC v Chelsea FC 02/01/1999 | £5.50 | |
| Queens Park Rangers FC v Huddersfield Town FC 02/01/1999 | £5.00 | |
| Southampton FC v Fulham FC 02/01/1999 | £3.50 | |
| Tottenham Hotspur FC v Watford FC 02/01/1999 | £3.00 | |
| Tottenham Hotspur FC v Watford FC 02/01/1999 | £5.00 | |
| West Ham United FC v Swansea City FC 02/01/1999 | £5.00 | |
| Sheffield Wednesday FC v Norwich City FC 03/01/1999 | £2.50 | |
| Manchester United FC v Middlesbrough FC 03/01/1999 | £7.00 | |
| Luton Town FC v Walsall FC 05/01/1999 | £5.50 | |
| Brighton & Hove Albion FC v Millwall FC 05/01/1999 | £9.50 | |
| Southampton FC v Charlton Athletic FC 09/01/1999 | £2.00 |