| Barnet FC v Darlington FC 09/01/1999 | View match | |
| Cardiff City FC v Darlington FC 23/01/1999 | View match | |
| Leyton Orient FC v Darlington FC 30/01/1999 | View match | |
| Darlington FC v Mansfield Town FC 06/02/1999 | View match | |
| Hartlepool United v Darlington FC 13/02/1999 | View match | |
| Darlington FC v Hull City FC 16/02/1999 | View match | |
| Darlington FC v Plymouth Argyle FC 20/02/1999 | View match | |
| Shrewsbury Town FC v Darlington FC 27/02/1999 | View match | |
| Swansea City FC v Darlington FC 09/03/1999 | View match | |
| Brighton & Hove Albion FC v Darlington FC 13/03/1999 | £6.50 | |
| Darlington FC v Southend United FC 20/03/1999 | View match | |
| Darlington FC v Carlisle United FC 23/03/1999 | View match |