| Luton Town FC v Chesterfield FC 26/12/1999 | £6.00 | |
| Bury FC v Burnley FC 26/12/1999 | £6.50 | |
| Birmingham City FC v Sheffield United FC 26/12/1999 | £2.00 | |
| West Bromwich Albion FC v Manchester City FC 26/12/1999 | £6.50 | |
| Fulham FC v Ipswich Town FC 26/12/1999 | £4.50 | |
| Brighton & Hove Albion FC v Barnet FC 26/12/1999 | £5.50 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.50 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.00 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.00 | |
| Southampton FC v Chelsea FC 26/12/1999 | £2.50 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.50 | |
| Tottenham Hotspur FC v Watford FC 26/12/1999 | £4.00 |