It represents the first opportunity for the Blues to put that disappointing performance against Wycombe to bed, following the postponement of Saturday’s trip to Accrington.
It also allows Danny Cowley to get much-needed minutes into his players’ legs ahead of this weekend’s important League One game against MK Dons.
But what does the head coach do with his line-up and formation with such a big game on the horizon?
Does he give his regulars starting berths to get that Wycombe performance out of their system – but risk losing some of them to injury?
Does the boss stick to his policy of giving his fringe players the chance to shine in the Trophy and keep faith with the side that beat Ipswich last time out?
And does he abandon the three-at-the-back system that was rolled out not-so-successfully at Adams Park?
There’s so many questions which only Cowley and his coaching team can really answer.
Nevertheless, here’s how we think Pompey will line up tonight as they look to book a quarter-final place in the Papa John’s Trophy...
5. Denver Hume - left-back
The former Sunderland man has started the past two Trophy games as he continues to build-up his fitness following injury. There's no reason why that shouldn't continue tonight, with Cowley no doubt looking to ramp up competition for regular left-back Conor Ogilvie. Photo: Jason Brown
6. Reeco Hackett - Right-wing
Hackett came off the bench against Wycombe and looked like the only outfield player who could cause the Chairboys any problems. He needs more regular game time to improve his consistency, so tonight's game represents the perfect opportunity. Owen Dale has been good for Pompey down the right, but perhaps Cowley needs to keep one eye on the future, with the winger potentially heading back to Blackpool in January. Photo: Simon Davies
7. Joe Morrell - central midfield 1
Pompey fans need to start seeing something from the midfielder with his season to date interrupted by injury, sickness and the World Cup. That should see him line up against Stevenage, with the Welsh international remaining on the bench at Wycombe just days after his return from Qatar. He needs game time ahead of a hectic festive period. Photo: Jason Brown
8. Jay Mingi - central midfield 2
Was brought off at half-time at Wycombe and will no doubt be determined to remind Pompey fans what he can bring to the table - especially with midfield competition for places heating up following Morrell's return and Tom Lowery and Louis Thompson closing in on their comebacks from injury. Photo: Jason Brown