| Saturday 7th August 1999 | |||
| Brighton and Hove A | 6-0 | Mansfield Town | |
| Carlisle United | 2-1 | Leyton Orient | |
| Cheltenham Town | 0-2 | Rochdale | |
| Chester City | 0-2 | Barnet | |
| Exeter City | 1-0 | Hull City | |
| Halifax Town | 0-1 | Darlington | |
| Lincoln City | 2-1 | Rotherham United | |
| Macclesfield Town | 1-0 | Northampton Town | |
| Peterborough United | 2-1 | Hartlepool United | |
| Shrewsbury Town | 1-2 | Torquay United | |
| Southend United | 2-1 | Plymouth Argyle | |
| York City | 1-0 | Swansea City | |
» English Division Three 1999-2000 : Results
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