2008–09 Football League Cup First round South

| Tie_no | Home_team | Score_1 | Away_team | Attendance |
|---|---|---|---|---|
| 1 | Coventry City | 3 – 1 | Aldershot Town | 9293 |
| 2 | Milton Keynes Dons | 1 – 0 | Norwich City | 6261 |
| 3 | Wycombe Wanderers | 0 – 4 | Birmingham City | 2735 |
| 4 | Brighton & Hove Albion | 4 – 0 | Barnet | 2571 |
| 5 | Gillingham | 0 – 1 | Colchester United | 2566 |
| 6 | Southend United | 0 – 0 | Cheltenham Town | 2998 |
| Cheltenham Town won 1 – 0 after extra time | Cheltenham Town won 1 – 0 after extra time | Cheltenham Town won 1 – 0 after extra time | Cheltenham Town won 1 – 0 after extra time | Cheltenham Town won 1 – 0 after extra time |