Pompey have been handed a trip to Ipswich in the third round of the FA Cup.
Paul Cook’s side have been drawn away to the Championship side following a 1-0 win against Accrington on Saturday.
The last time the Blues played the Tractor Boys in the competition, they went on to the win the Cup at Wembley.
Pompey won 1-0 at Portman Road in the 2007-08 season thanks to a David Nugent goal.
The third-round ties will be played between January 8-11.