2008–09 FA Cup Qualifying Rounds First qualifying round 2

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| 59 | Billericay Town | 4–1 | FC Clacton | 337 |
| 60 | Oxhey Jets | 1–5 | Dulwich Hamlet | 148 |
| 61 | Hemel Hempstead Town | 1–1 | Harrow Borough | 199 |
| 62 | Thamesmead Town | 2–1 | Great Wakering Rovers | 78 |
| 63 | Metropolitan Police | 0–3 | Corby Town | 140 |
| 64 | Wingate and Finchley | 2–0 | Witham Town | 115 |
| 65 | Stotfold | 0–3 | Leighton Town | 101 |
| 66 | Hitchin Town | 5–0 | Concord Rangers | 225 |
| 67 | Leyton | 2–4 | Brackley Town | 80 |
| 68 | Canvey Island | 1–5 | Dunstable Town | 312 |
| 69 | Raunds Town | 0–3 | Ashford Town (Middx) | 154 |
| 70 | Heybridge Swifts | 1–1 | Uxbridge | 145 |
| 71 | Cheshunt | 0–3 | Staines Town | 236 |
| 72 | Saffron Walden Town | 0–2 | AFC Hornchurch | 337 |