| Scunthorpe United FC v Bury FC 18/12/1999 | £6.00 | |
| Manchester City FC v Swindon Town FC 18/12/1999 | £5.00 | |
| Queens Park Rangers FC v Charlton Athletic FC 18/12/1999 | £6.50 | |
| Sunderland FC v Southampton FC 18/12/1999 | £4.00 | |
| Crystal Palace FC v Fulham FC 18/12/1999 | £3.00 | |
| Middlesbrough FC v Tottenham Hotspur FC 18/12/1999 | £4.50 | |
| Swansea City FC v Brighton & Hove Albion FC 18/12/1999 | £7.50 | |
| Chelsea FC v Leeds United FC 19/12/1999 | £3.00 | |
| Luton Town FC v Fulham FC 21/12/1999 | £6.00 | |
| Newcastle United FC v Tottenham Hotspur FC 22/12/1999 | £4.50 | |
| Sheffield Wednesday FC v Middlesbrough FC 26/12/1999 | £4.00 | |
| Wimbledon v West Ham United FC 26/12/1999 | £6.50 |