| Tranmere Rovers FC v Wolverhampton Wanderers FC 27/11/1999 | View match | |
| Tranmere Rovers FC v Barnsley FC 30/11/1999 | View match | |
| Bolton Wanderers FC v Tranmere Rovers FC 04/12/1999 | View match | |
| Tranmere Rovers FC v West Ham United FC 11/12/1999 | £7.50 | |
| Tranmere Rovers FC v Middlesbrough FC 14/12/1999 | View match | |
| Tranmere Rovers FC v Norwich City FC 17/12/1999 | View match | |
| Walsall FC v Tranmere Rovers FC 26/12/1999 | View match | |
| Tranmere Rovers FC v Swindon Town FC 28/12/1999 | View match | |
| Fulham FC v Tranmere Rovers FC 03/01/2000 | £4.00 | |
| Tranmere Rovers FC v Sunderland FC 08/01/2000 | View match | |
| Bolton Wanderers FC v Tranmere Rovers FC 12/01/2000 | £7.50 | |
| Tranmere Rovers FC v Stockport County FC 15/01/2000 | View match |