Pompey have been drawn at home to League One outfit Peterborough United in the first round of the Capital One Cup.
The tie will be played at Fratton Park in the week beginning August 11.
The sides last met when they were both in the Championship during the 2011/12 campaign.
Pompey were beaten 3-2 at Fratton Park before gaining revenge with a 3-0 victory at London Road.
There have been three previous League Cup clashes between the Blues and the Posh.
Each side won a two-legged tie before Pompey triumphed 2-0 in a one-off match in 2002.
Peterborough made a roaring start to last season’s Capital One Cup, beating Colchester 5-1 and Reading 6-0 before going down 2-0 at Premier League Sunderland.
Pompey, meanwhile, fell at the first hurdle with a 1-0 defeat at Bournemouth.
Capital One Cup first round draw
Oldham Athletic v Middlesbrough
Shrewsbury Town v Blackpool
Sheffield Wednesday v Notts County
Tranmere Rovers v Nottingham Forest
Leeds United v Accrington Stanley
Bolton Wanderers v Bury
Rochdale v Preston North End
Rotherham United v Fleetwood Town
Carlisle United v Derby County
Port Vale v Hartlepool United
Morecambe v Bradford City
Barnsley v Crewe Alexandra
Chesterfield v Huddersfield Town
Blackburn Rovers v Scunthorpe United
Burton Albion v Wigan Athletic
York City v Doncaster Rovers
Sheffield United v Mansfield Town
Reading v Newport County
Bristol City v Oxford United
Brighton & Hove Albion v Cheltenham Town
Coventry City v Cardiff City
Luton Town v Swindon Town
Dagenham & Redbridge v Brentford
Charlton Athletic v Colchester United
Crawley Town v Ipswich Town
Wolverhampton Wanderers v Northampton Town
Yeovil Town v Gillingham
Milton Keynes Dons v AFC Wimbledon
Exeter City v AFC Bournemouth
Stevenage v Watford
Plymouth Argyle v Leyton Orient
Birmingham City v Cambridge United
POMPEY v Peterborough United
Millwall v Wycombe Wanderers
Southend United v Walsall