Football League Cup 2008-09
Sponsored by Carling
First Round
Northern Section
- Preston North End 2-0 Chesterfield
- Chester City 2-5 Leeds United
- Leicester City 1-0 Stockport County
- Sheffield United - Port Vale
- Grimsby Town 2-0 Tranmere Rovers
- Crewe Alexandra 2-0 Barnsley
- Hartlepool United 3-0 Scunthorpe United
- Derby County 3-1 Lincoln City
- Notts County 1-0 Doncaster Rovers
- Sheffield Wednesday 2-2 Rotherham United (Rotherham won 5-3 on penalties)
- Shrewsbury Town 0-1 Carlisle United
- Wolverhampton Wanderers 3-2 Accrington Stanley
- Bury 0-2 Burnley
- Rochdale 0-0 Oldham Athletic (Oldham won 4-1 on penalties)
- Nottingham Forest - Morecambe
- Huddersfield Town 4-0 Bradford City
- Macclesfield Town 2-0 Blackpool
- Walsall 1-2 Darlington
Southern Section
- Coventry City - Aldershot Town
- Milton Keynes Dons 1-0 Norwich City
- Wycombe Wanderers - Birmingham City
- Brighton & Hove Albion 4-0 Barnet
- Gillingham 0-1 Colchester United
- Southend United 0-1 Cheltenham Town
- Swansea City 2-0 Brentford
- Luton Town 2-0 Plymouth Argyle
- Exeter City 1-3 Southampton
- Watford 1-0 Bristol Rovers
- A F C Bournemouth 1-2 Cardiff City
- Bristol City 2-1 Peterborough United
- Charlton Athletic 0-1 Yeovil Town
- Millwall 0-1 Northampton Town
- Swindon Town 2-3 Queens Park Rangers
- Crystal Palace 2-1 Hereford United
- Dagenham & Redbridge 1-2 Reading
- Ipswich Town 4-1 Leyton Orient
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