Blues on the road in first roundPompey have been drawn away to League One side Coventry in the first round of the EFL Cup.
The tie will be played at the Ricoh Arena in the week beginning August 8.
The sides have not met since Jed Wallace and Patrick Agyemang scored in a 2-0 League One triumph at Fratton Park in March 2013.
Pompey’s last trip to the Ricoh Arena came earlier that season, with Izale McLeod’s equaliser securing a 1-1 draw.
And fans will have fond memories of their most recent cup visit to the Sky Blues back in 2010.
Aaron Mokoena netted in the last minute of extra-time to send Pompey into the fourth round of the FA Cup – and they went on to reach the final at Wembley.
There have been three previous clashes between the teams in the League Cup, with the Blues coming out on top in 1960 and 1962, while Coventry prevailed in 1968.
Paul Cook’s men knocked out Championship side Derby in the first round of last season’s competition before narrowly losing to Reading.
Coventry, meanwhile, fell at the first hurdle, losing on penalties at Rochdale following a 1-1 draw.
EFL Cup first round draw
Peterborough United v AFC Wimbledon
Bristol Rovers v Cardiff City
Coventry City v POMPEY
Luton Town v Aston Villa
Brighton & Hove Albion v Colchester United
Cheltenham Town v Charlton Athletic
Birmingham City v Oxford United
Southend United v Gillingham
Wolverhampton Wanderers v Crawley Town
Leyton Orient v Fulham
Ipswich Town v Stevenage
Wycombe Wanderers v Bristol City
Walsall v Yeovil Town
Exeter City v Brentford
Queens Park Rangers v Swindon Town
Barnet v Millwall
Reading v Plymouth Argyle
Newport County v Milton Keynes Dons
Carlisle United v Port Vale
Rotherham United v Morecambe
Accrington Stanley v Bradford City
Rochdale v Chesterfield
Mansfield Town v Blackburn Rovers
Barnsley v Northampton Town
Cambridge United v Sheffield Wednesday
Derby County v Grimsby Town
Oldham Athletic v Wigan Athletic
Scunthorpe United v Notts County
Doncaster Rovers v Nottingham Forest
Burton Albion v Bury
Fleetwood Town v Leeds United
Sheffield United v Crewe Alexandra
Shrewsbury Town v Huddersfield Town
Preston North End v Hartlepool United
Blackpool v Bolton Wanderers