Pompey have been drawn away to Championship side QPR in the second round of the Carabao Cup.
The tie will be played at Loftus Road in the week beginning August 26.
There were two meetings between the sides last season, with a 1-1 draw at Fratton Park in the fourth round of the FA Cup.
It was the Londoners who came out on top in the replay, however, courtesy of a couple of second half goals.
But you have to go back to the 1981/82 campaign to find the last League Cup clash, with QPR easing to a 7-2 aggregate triumph.
Pompey reached the second round of this season's competition with a 3-0 defeat over another Championship outfit, Birmingham, at Fratton Park.
Their next opponents scored a late penalty to draw 3-3 against Bristol City on home soil, then triumphed 5-4 in the resulting shoot-out.
"The league is everything for us, but cup competitions are a nice distraction and it’ll be great to pit our wits against another Championship side."
Pompey assistant manager Joe Gallen said: "I always enjoy facing a side from a higher division because we start as underdogs and it’s a great opportunity to test ourselves.
"The Birmingham game was an enjoyable one and we’ll look forward to facing QPR when the tie comes around.
"The league is everything for us, but cup competitions are a nice distraction and it’ll be great to pit our wits against another Championship side."
The Blues fell at the first hurdle against AFC Wimbledon last term, while Rangers got to round three before losing at Blackpool.
Carabao Cup Round Two – South |
Plymouth Argyle v Reading |
Crawley Town v Norwich City |
Newport County v West Ham United |
Oxford United v Millwall |
Watford v Coventry City |
Swansea City v Cambridge United |
Cardiff City v Luton Town |
Bristol Rovers v Brighton & Hove Albion |
Crystal Palace v Colchester United |
Fulham v Southampton |
AFC Bournemouth v Forest Green Rovers |
Southend United v Milton Keynes Dons |
Queens Park Rangers v POMPEY |
Carabao Cup Round Two – North |
Crewe Alexandra v Aston Villa |
Lincoln City v Everton |
Leeds United v Stoke City |
Sheffield United v Blackburn Rovers |
Rotherham United v Sheffield Wednesday or Bury |
Newcastle United v Leicester City |
Burton Albion v Morecambe |
Burnley v Sunderland |
Nottingham Forest v Derby County |
Grimsby Town v Macclesfield Town |
Preston North End v Hull City |
Rochdale v Carlisle United |