2008–09 FA Cup First Round Proper Group B

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| Luton Town won 4–2 on penalties | Luton Town won 4–2 on penalties | Luton Town won 4–2 on penalties | Luton Town won 4–2 on penalties | Luton Town won 4–2 on penalties |
| 37 | Crewe Alexandra | 1 – 0 | Ebbsfleet United | 2593 |
| 38 | Eastwood Town | 2 – 1 | Brackley Town | 960 |
| 39 | Leeds United | 1 – 1 | Northampton Town | 9531 |
| replay | Northampton Town | 2 – 5 | Leeds United | 3960 |
| 40 | Harlow Town | 0 – 2 | Macclesfield Town | 2149 |