2008–09 FA Cup First Round Proper Group A

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| 1 | Colchester United | 0 – 1 | Leyton Orient | 4600 |
| 2 | Havant & Waterlooville | 1 – 3 | Brentford | 1631 |
| 3 | Blyth Spartans | 3 – 1 | Shrewsbury Town | 2742 |
| 4 | Sutton United | 0 – 1 | Notts County | 2041 |
| 5 | Torquay United | 2 – 0 | Evesham United | 2275 |
| 6 | Oxford United | 0 – 0 | Dorchester Town | 3196 |
| replay | Dorchester Town | 1 – 3† | Oxford United | 1474 |
| 7 | Bury | 0 – 1 | Gillingham | 2161 |
| 8 | AFC Wimbledon | 1 – 4 | Wycombe Wanderers | 4528 |
| 9 | Chester City | 0 – 3 | Millwall | 1932 |
| 10 | Carlisle United | 1 – 1 | Grays Athletic | 3921 |