| Sheffield Wednesday FC v Bristol City FC 11/12/1999 | £4.00 | |
| Tranmere Rovers FC v West Ham United FC 11/12/1999 | £7.50 | |
| Wrexham FC v Middlesbrough FC 11/12/1999 | £6.99 | |
| Tottenham Hotspur FC v Newcastle United FC 12/12/1999 | £5.00 | |
| Arsenal FC v Blackpool FC 13/12/1999 | £2.00 | |
| Arsenal FC v Blackpool FC 13/12/1999 | £4.50 | |
| Arsenal FC v Wimbledon 18/12/1999 | £5.00 | |
| Arsenal FC v Wimbledon 18/12/1999 | £6.50 | |
| Arsenal FC v Wimbledon 18/12/1999 | £4.00 | |
| Scunthorpe United FC v Bury FC 18/12/1999 | £6.00 | |
| Middlesbrough FC v Tottenham Hotspur FC 18/12/1999 | £4.50 | |
| Swansea City FC v Brighton & Hove Albion FC 18/12/1999 | £7.50 |