| Chesterfield FC v Bury FC 28/12/1999 | £6.50 | |
| Chelsea FC v Sheffield Wednesday FC 29/12/1999 | £3.00 | |
| Aston Villa FC v Tottenham Hotspur FC 29/12/1999 | £4.50 | |
| Southampton FC v Bradford City FC 03/01/2000 | £4.00 | |
| Southampton FC v Bradford City FC 03/01/2000 | £2.00 | |
| Tottenham Hotspur FC v Liverpool FC 03/01/2000 | £5.00 | |
| Charlton Athletic FC v Nottingham Forest FC 03/01/2000 | £5.50 | |
| Luton Town FC v Scunthorpe United FC 03/01/2000 | £6.00 | |
| Newcastle United FC v West Ham United FC 03/01/2000 | £5.00 | |
| Fulham FC v Tranmere Rovers FC 03/01/2000 | £4.00 | |
| Brighton & Hove Albion FC v Exeter City FC 03/01/2000 | £6.00 | |
| Coventry City FC v Chelsea FC 04/01/2000 | £3.50 |