Pompey have been drawn away to League Two side Newport in the second round of the Carabao Cup.
The tie will be played at Rodney Parade in the week commencing August 22, with a confirmed date and ticket details to be announced in due course.
It means there will be a quick return to south Wales for Danny Cowley's men, who enjoyed a 3-0 victory at Cardiff to seal their progress on Tuesday night.
Pompey have not faced the Exiles since both sides occupied the fourth tier during the 2016/17 campaign.
They won both matches that season on the way to winning the title, including a dramatic 3-2 triumph at Rodney Parade on Boxing Day.
| Carabao Cup Round Two – Southern Section |
| Stevenage v Peterborough United |
| Norwich City v AFC Bournemouth |
| Newport County v POMPEY |
| Oxford United v Crystal Palace |
| Watford v Milton Keynes Dons |
| Colchester United v Brentford |
| Wycombe Wanderers v Bristol City |
| Walsall v Charlton Athletic |
| Crawley Town v Fulham |
| Cambridge United v Southampton |
| Gillingham v Exeter City |
| Forest Green Rovers v Brighton & Hove Albion |
| Carabao Cup Round Two – Northern Section |
| Bolton Wanderers v Aston Villa |
| Derby County v West Bromwich Albion |
| Wolverhampton Wanderers v Preston North End |
| Leeds United v Barnsley |
| Fleetwood Town v Everton |
| Sheffield Wednesday v Rochdale |
| Tranmere Rovers v Newcastle |
| Rotherham United v Morecambe |
| Barrow v Lincoln City |
| Stockport County v Leicester City |
| Bradford City v Blackburn Rovers |
| Grimsby Town v Nottingham Forest |
| Shrewsbury Town v Burnley |