| Ipswich Town FC v Grimsby Town FC 09/01/1999 | View match | |
| Sunderland FC v Ipswich Town FC 17/01/1999 | View match | |
| Everton FC v Ipswich Town FC 23/01/1999 | View match | |
| Ipswich Town FC v Port Vale FC 30/01/1999 | View match | |
| Bury FC v Ipswich Town FC 06/02/1999 | £6.50 | |
| Bradford City FC v Ipswich Town FC 13/02/1999 | View match | |
| Ipswich Town FC v Oxford United FC 20/02/1999 | View match | |
| Bristol City FC v Ipswich Town FC 27/02/1999 | View match | |
| Ipswich Town FC v Watford FC 02/03/1999 | View match | |
| Ipswich Town FC v Tranmere Rovers FC 06/03/1999 | View match | |
| Crystal Palace FC v Ipswich Town FC 09/03/1999 | View match | |
| Ipswich Town FC v Huddersfield Town FC 13/03/1999 | View match |