| Crystal Palace FC v Ipswich Town FC 07/12/1999 | £2.50 | |
| Ipswich Town FC v Southampton FC 13/12/1999 | View match | |
| Ipswich Town FC v West Bromwich Albion FC 18/12/1999 | View match | |
| Fulham FC v Ipswich Town FC 26/12/1999 | £4.50 | |
| Ipswich Town FC v Stockport County FC 28/12/1999 | View match | |
| Port Vale FC v Ipswich Town FC 03/01/2000 | View match | |
| Ipswich Town FC v Swindon Town FC 15/01/2000 | View match | |
| Bolton Wanderers FC v Ipswich Town FC 22/01/2000 | View match | |
| Ipswich Town FC v Sheffield United FC 29/01/2000 | View match | |
| Barnsley FC v Ipswich Town FC 05/02/2000 | View match | |
| Ipswich Town FC v Huddersfield Town FC 12/02/2000 | View match | |
| Crewe Alexandra FC v Ipswich Town FC 19/02/2000 | View match |