| Sheffield United FC v Ipswich Town FC 28/08/1999 | View match | |
| Ipswich Town FC v Barnsley FC 30/08/1999 | View match | |
| Portsmouth FC v Ipswich Town FC 11/09/1999 | View match | |
| Crewe Alexandra FC v Ipswich Town FC 14/09/1999 | View match | |
| Ipswich Town FC v Birmingham City FC 18/09/1999 | View match | |
| Ipswich Town FC v Crewe Alexandra FC 21/09/1999 | View match | |
| Ipswich Town FC v Manchester City FC 26/09/1999 | £5.00 | |
| Grimsby Town FC v Ipswich Town FC 02/10/1999 | View match | |
| Ipswich Town FC v Queens Park Rangers FC 16/10/1999 | View match | |
| Ipswich Town FC v Charlton Athletic FC 19/10/1999 | View match | |
| Walsall FC v Ipswich Town FC 23/10/1999 | View match | |
| Manchester City FC v Ipswich Town FC 27/10/1999 | £5.00 |