The Capital One Cup draw will bring back memories of one of Leicester City's greatest humiliations when they visit Wycombe Wanderers.
Roy Essandoh's last minute winner which knocked Premier League City out of the FA Cup at Filbert Street in 2001 is the only previous meeting between the two clubs.
City were odds on to beat the Second Division side and cruise into the semi-finals, and Wanderers were so ravaged by injury they advertised for a striker on the internet and recruited Essendoh on a trialist's contract.
The substitute completed his Roy of the Rovers feat after coming on as a substitute and the result went down in the history books as one of the FA Cup's most infamous cup shocks.
City went on a club record run of nine straight defeats after that loss.
The game will be played the week commencing August 5.
The other fixtures are:
Bury v Crewe Alexandra
Shrewsbury Town v Bolton Wanderers
Middlesbrough v Accrington Stanley
Doncaster Rovers v Rochdale
Preston North End v Blackpool
Barnsley v Scunthorpe United
Tranmere Rovers v Mansfield Town
York City v Burnley
Notts County v Fleetwood Town
Sheffield United v Burton Albion
Oldham Athletic v Derby County
Carlisle United v Blackburn Rovers
Morecambe v Wolverhampton Wanderers
Nottingham Forest v Hartlepool United
Leeds United v Chesterfield
Huddersfield Town v Bradford City
Rotherham United v Sheffield Wednesday
Port Vale v Walsall
Gillingham v Bristol City
AFC Bournemouth v Portsmouth
Brentford v Dagenham and Redbridge
Exeter City v Queens Park Rangers
Charlton Athletic v Oxford United
Southend United v Yeovil Town
Millwall v AFC Wimbledon
Swindon Town v Torquay United
Birmingham City v Plymouth Argyle
Stevenage v Ipswich Town
Cheltenham Town v Crawley Town
Bristol Rovers v Watford
Northampton Town v Milton Keynes Dons
Leyton Orient v Coventry City
Colchester United v Peterborough United
Brighton v Newport County
