| Northampton Town FC v Darlington FC 28/12/1999 | View match | |
| Chester City FC v Darlington FC 08/01/2000 | View match | |
| Macclesfield Town FC v Darlington FC 15/01/2000 | View match | |
| Darlington FC v York City FC 18/01/2000 | View match | |
| Brighton & Hove Albion FC v Darlington FC 29/01/2000 | £6.00 | |
| Darlington FC v Peterborough United FC 06/02/2000 | View match | |
| Exeter City FC v Darlington FC 12/02/2000 | View match | |
| Darlington FC v Southend United FC 19/02/2000 | View match | |
| Mansfield Town FC v Darlington FC 26/02/2000 | View match | |
| Darlington FC v Rochdale FC 04/03/2000 | View match | |
| Darlington FC v Barnet FC 07/03/2000 | View match | |
| Leyton Orient FC v Darlington FC 11/03/2000 | View match |