| Tottenham Hotspur FC v Watford FC 26/12/1999 | £4.50 | |
| Charlton Athletic FC v Crystal Palace FC 26/12/1999 | £4.50 | |
| Charlton Athletic FC v Crystal Palace FC 26/12/1999 | £2.00 | |
| Arsenal FC v Leeds United FC 28/12/1999 | £3.00 | |
| Arsenal FC v Leeds United FC 28/12/1999 | £5.00 | |
| Liverpool FC v Wimbledon 28/12/1999 | £4.00 | |
| Liverpool FC v Wimbledon 28/12/1999 | £5.00 | |
| Manchester City FC v Grimsby Town FC 28/12/1999 | £5.00 | |
| Queens Park Rangers FC v Crewe Alexandra FC 28/12/1999 | £5.00 | |
| Rotherham United FC v Brighton & Hove Albion FC 28/12/1999 | £7.50 | |
| West Ham United FC v Derby County FC 28/12/1999 | £5.50 | |
| Watford FC v Southampton FC 28/12/1999 | £6.50 |