And it’s a game that promises to stretch Danny Cowley’s options, with the Blues boss keen to give some of his fringe players a chance to shine.
There’ll be a few regulars asked to step up again given the ongoing injury problems the Fratton Park outfit have.
Indeed, the luxury of making the wholesale changes that were evident earlier in the competition are a thing of the past, with the likes of Tomy Lowery, Michael Jacobs and Joe Rafferty out injured, Joe Morrell currently at the World Cup and Joe Pigott ineligible to feature against his parent club.
Cowley still has enough room for manoeuvre – just – as he attempts to keep all members of his squad happy.
But with a real desire to progress in the Trophy, what kind of side can we realistically expect at Portman Road?
Here’s how we think Pompey will line up tonight...
5. Denver Hume - left-back
Another chance for the former Sunderland man to build up his match minutes and make up for lost time following back and calf injures that stretch back to March. Has shown promise on his return - now the Blues need to get him fully firing again. Photo: Jason Brown
6. Owen Dale - right-wing
Following his performance against Derby last time out, Dale probably deserves a night off to keep him fresh. But with the on-loan Blackpool winger unlikely to be available for Saturday's FA Cup game against MK Dons, there's a chance he could start at Portman Road give to the Blues some attacking impetus. Photo: Jason Brown
7. Ryan Tunnicliffe - central midfield 1
Six consecutive appearances came to an end against Derby last Friday night as Danny Cowley preferred to pair Jay Mingi with Marlon Pack in the centre of midfield. Pack will likely be rested for tonight's game, and with Tom Lowery, Joe Morrell and Louis Thompson all unavailable, Tunnicliffe could be asked to step up again. Photo: Paul Thompson
8. Jay Mingi - central midfield 2
A bit like Swanson, Danny Cowley will be reluctant to overuse Mingi given the squad's injury record in recent weeks. But the more games the young midfielder gets the better for the Blues. Photo: Jason Brown