| Crewe Alexandra FC v Grimsby Town FC 27/08/1999 | View match | |
| Birmingham City FC v Crewe Alexandra FC 30/08/1999 | View match | |
| Norwich City FC v Crewe Alexandra FC 11/09/1999 | View match | |
| Crewe Alexandra FC v Ipswich Town FC 14/09/1999 | View match | |
| Crewe Alexandra FC v Swindon Town FC 18/09/1999 | View match | |
| Ipswich Town FC v Crewe Alexandra FC 21/09/1999 | View match | |
| Fulham FC v Crewe Alexandra FC 25/09/1999 | £4.00 | |
| Crewe Alexandra FC v Tranmere Rovers FC 03/10/1999 | View match | |
| Crewe Alexandra FC v Sheffield United FC 09/10/1999 | View match | |
| Tottenham Hotspur FC v Crewe Alexandra FC 13/10/1999 | £5.00 | |
| Tottenham Hotspur FC v Crewe Alexandra FC 13/10/1999 | £3.50 | |
| Stockport County FC v Crewe Alexandra FC 16/10/1999 | View match |