Pompey have been drawn at home to Scunthorpe in the quarter-finals of the Leasing.com Trophy.
The League Two side will visit Fratton Park in the week commencing January 20.
It will be the first time the sides have met in this competition, although the Blues won 2-0 in a league meeting on the south coast last March.
The Iron were relegated at the end of that season and currently sit 14th in the fourth tier standings – 10 points adrift of the play-off spots.
Paul Hurst's side have already seen off Blackpool and Manchester City U21s in the knockout stages to progress this far.
Scunthorpe have never previously won the competition – in any of its guises – but did get to the final in 2009, losing to Luton.
A confirmed date for the tie and ticket information will be announced in due course.
|Leasing.com Trophy quarter-final draw|
|Exeter City v Stevenage|
|Salford City v Accrington Stanley|
|POMPEY v Scunthorpe United|
|Newport County v Leicester City U21|