Pompey will travel to Premier League side Brighton in the second round of the Carabao Cup.
The tie will be played at the Amex Stadium in the week commencing September 14.
Whoever comes out on top will then face a trip to either Derby or Preston in the third round a week later.
It will be the first competitive meeting between the south coast sides since both were residents of the Championship during the 2011/12 campaign.
The Seagulls emerged victorious in both contests that term, including a 2-0 triumph in East Sussex.
You have to go all the way back to 1970 to find the last time they clashed in the League Cup, with Brighton enjoying a narrow win that year.
But it was a different story in 1962, when a Ron Saunders treble and Roy Smith brace saw Albion trounced 5-1 on their own patch in the first round.
Brighton enter the competition at this stage because of their top-flight status, while Pompey won at Stevenage on penalties in the first round.
Kenny Jackett's troops could come up against a familiar face, with Blues academy graduate Adam Webster now plying his trade at the Amex Stadium.
|Carabao Cup Round Two – South|
|West Ham United v Charlton Athletic|
|Ipswich Town v Fulham|
|Oxford United v Watford|
|AFC Bournemouth v Crystal Palace|
|Leyton Orient v Plymouth Argyle|
|Southampton v Brentford|
|Bristol City v Northampton Town|
|Reading v Luton Town|
|Millwall v Cheltenham Town|
|Brighton & Hove Albion v POMPEY|
|Newport County v Cambridge United|
|Gillingham v Coventry City|
|Carabao Cup Round Two – North|
|Burnley v Sheffield United|
|Burton Albion v Aston Villa|
|Bradford City v Lincoln City|
|Leeds United v Hull City|
|Everton v Salford City|
|Wolverhampton Wanderers v Stoke City|
|Fleetwood Town v Port Vale|
|Rochdale v Sheffield Wednesday|
|West Bromwich Albion v Harrogate Town|
|Middlesbrough v Barnsley|
|Derby County v Preston North End|
|Newcastle United v Blackburn Rovers|
|Morecambe v Oldham Athletic|
|Carabao Cup Round Three|
|Bradford City or Lincoln City v Liverpool|
|Bristol City or Northampton Town v Burton Albion or Aston Villa|
|Morecambe or Oldham Athletic v Newcastle United or Blackburn Rovers|
|Reading or Luton Town v Manchester United|
|Derby County or Preston North End v Brighton & Hove Albion or POMPEY|
|Ipswich Town or Fulham v Rochdale or Sheffield Wednesday|
|Manchester City v AFC Bounemouth or Crystal Palace|
|Millwall or Cheltenham Town v Burnley or Sheffield United|
|Chelsea v Middlesbrough or Barnsley|
|Wolverhampton Wanderers or Stoke City v Gillingham or Coventry City|
|Leicester City v Arsenal|
|West Bromwich Albion or Harrogate Town v Southampton or Brentford|
|Newport County or Cambridge United v Oxford United or Watford|
|Fleetwood Town or Port Vale v Everton or Salford City|
|Leyton Orient or Plymouth Argyle v Tottenham Hotspur|
|West Ham United or Charlton Athletic v Leeds United or Hull City|