Pompey have been drawn at home to League Two side Exeter in the semi-finals of the Leasing.com Trophy.
The tie will be played at Fratton Park in the week commencing February 17 and screened live on Sky Sports.
It was the Grecians who came out on top when the sides last met in this competition back in September 2015.
An inexperienced Blues side were beaten 2-0 at St James Park in the first round, with Ryan Harley and Alex Nicholls on target.
The most recent encounters took place in Pompey's title-winning season a few years ago, with each club winning 1-0 on the other's patch.
Exeter are currently sitting second in the League Two table and have not lost any of their past 10 matches in all competitions.
They topped Southern Group E of the Leasing.com Trophy with a maximum haul of points, then saw off Oxford, Ipswich and Stevenage to reach the last four.
Pompey are the current holders and looking to become the first side to successfully defend the silverware.
A confirmed date for the fixture and ticket information will be announced in due course.
|Leasing.com Trophy semi-finals
|POMPEY v Exeter City
|Newport County or Leicester City U21 v Salford City