2008–09 FA Cup Qualifying Rounds First qualifying round 2

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| 89 | Merstham | 2–1 | Whitstable Town | 130 |
| 90 | Hythe Town | 0–0 | VCD Athletic | 143 |
| 91 | Tonbridge Angels | 1–2 | Dover Athletic | 795 |
| 92 | Chipstead | 1–0 | Chatham Town | 85 |
| 93 | Maidstone United | 2–1 | Tooting & Mitcham United | 355 |
| 94 | Bracknell Town | 2–0 | Oxford City | 111 |
| 95 | Aylesbury Vale | 2–0 | Downton | 70 |
| 96 | Shortwood United | 3–2 | Didcot Town | 124 |
| 97 | Farnborough | 1–0 | Slough Town | 571 |
| 98 | Fleet Town | 3–0 | Cowes Sports | 141 |
| 99 | Newport Pagnell Town | 2–1 | Marlow | 148 |
| 100 | Aylesbury United | 1–0 | Almondsbury Town | 163 |
| 101 | Chalfont St Peter | 5–3 | Gloucester City | 145 |
| 102 | Chippenham Town | 2–0 | Banbury United | 269 |
| 103 | Calne Town | 0–5 | Bashley | 125 |