Pompey have been drawn away to fellow League One side Peterborough in the third round of the Papa John's Trophy.
The tie is scheduled to take place at London Road in the week commencing January 11.
It was only a week ago that the sides met at Fratton Park for a league fixture, with goals from Jack Whatmough and Tom Naylor securing a 2-0 victory.
A late goal from David Wheeler was enough to settle a quarter-final tie on the south coast in January 2019, with Kenny Jackett's men going on to lift the silverware at Wembley.
That was Pompey's only previous success in the competition – although they are still waiting to play last season's final against Salford.
Peterborough have also enjoyed one triumph at the national stadium, beating Chesterfield 3-1 in the 2014 showpiece.
|Papa John's Trophy Round Three – South|
|Bristol Rovers v AFC Wimbledon|
|Northampton Town v Milton Keynes Dons|
|Oxford United v Cambridge United|
|Peterborough United v POMPEY|
|Papa John's Trophy Round Three – North|
|Tranmere Rovers v Leicester City U21|
|Lincoln City v Accrington Stanley|
|Sunderland v Port Vale|
|Hull City v Fleetwood Town|