2008–09 FA Cup First Round Proper Group B

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| 21 | Morecambe | 2 – 1 | Grimsby Town | 1713 |
| 22 | Huddersfield Town | 3 – 4 | Port Vale | 6942 |
| 23 | Alfreton Town | 4 – 2 | Bury Town | 1060 |
| 24 | Kidderminster Harriers | 1 – 0 | Cambridge United | 1717 |
| 25 | Leicester City | 3 – 0 | Stevenage Borough | 7586 |
| 26 | Milton Keynes Dons | 1 – 2 | Bradford City | 5542 |
| 27 | Darlington | 0 – 0 | Droylsden | 2479 |
| replay | Droylsden | 1 – 0 | Darlington | 1672 |
| 28 | Chesterfield | 3 – 1 | Mansfield Town | 6612 |
| 29 | AFC Telford United | 2 – 2 | Southend United | 3631 |
| replay | Southend United | 2 – 0 | AFC Telford United | 4415 |