The Blades will host the Recreation Ground club, presumably on Tuesday, 14 August as Sheffield Wednesday have been handed an away tie at local rivals Rotherham United.
It should prove to be a memorable reunion for three of the Spirites strikers; Wayne Allison, Paul Shaw and new signing Jack Lester are all former Sheffield United strikers.
Sheffield United have only once met Chesterfield in the League Cup, the Blades won 3-1 at Bramall Lane on 10 September 1974.
:: Carling Cup First Round Draw ::
Wolverhampton Wanderers v Bradford City
Grimsby Town v Burnley
Rochdale v Stoke City
Scunthorpe United v Hartlepool United
Port Vale v Wrexham
Crewe Alexandra v Hull City
Chester City v Nottingham Forest
Sheffield United v Chesterfield
Rotherham United v Sheffield Wednesday
Barnsley v Darlington
Bury v Carlisle United
Doncaster Rovers v Lincoln City
Preston North End v Morecambe
Stockport County v Tranmere Rovers
Accrington Stanley v Leicester City
Macclesfield Town v Leeds United
Oldham Athletic v Mansfield Town
Blackpool v Huddersfield Town
Watford v Gillingham
Swindon Town v Charlton Athletic
Milton Keynes Dons v Ipswich Town
Southend United v Cheltenham Town
Norwich City v Barnet
Shrewsbury Town v Colchester United
Cardiff City v Brighton & Hove Albion
Swansea City v Walsall
Brentford v Bristol City
Bristol Rovers v Crystal Palace
West Bromwich Albion v Bournemouth
Peterborough United v Southampton
Hereford United v Yeovil Town
Queens Park Rangers v Leyton Orient
Northampton Town v Millwall
Dagenham & Redbridge v Luton Town
Plymouth Argyle v Wycombe Wanderers
Coventry City v Nott's County
Ties to be played week commencing Monday, 13 August 2007.