| Arsenal FC v Everton FC 16/10/1999 | £2.00 | |
| Middlesbrough FC v West Ham United FC 17/10/1999 | £5.00 | |
| Fulham FC v Wolverhampton Wanderers FC 19/10/1999 | £11.50 | |
| Portsmouth FC v Walsall FC 19/10/1999 | £2.50 | |
| Birmingham City FC v Manchester City FC 19/10/1999 | £8.00 | |
| Luton Town FC v Wycombe Wanderers FC 19/10/1999 | £5.00 | |
| Arsenal FC v Barcelona 19/10/1999 | £4.50 | |
| Reading FC v Bury FC 20/10/1999 | £6.50 | |
| Cheltenham Town FC v Brighton & Hove Albion FC 23/10/1999 | £5.00 | |
| Bury FC v AFC Bournemouth 23/10/1999 | £5.00 | |
| Queens Park Rangers FC v Portsmouth FC 23/10/1999 | £5.00 | |
| Sheffield Wednesday FC v Coventry City FC 23/10/1999 | £4.00 |