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...
1. Josh Oluwayemi - goalkeeper
Danny Cowley reiterated in his pre-match press conference that he still sees the Papa John's Trophy as a competition that can be used for development purposes. As a result, we can expect Oluwayemi to start, with the Trophy his only real source of match action as he plays understudy to Josh Griffiths. Has proven to be a reliable presence, too, when he's come in. Photo: Jason Brown
2. Zak Swanson - right-back
The former Arsenal youngster missed the Wycombe game with a stomach muscle injury, forcing Danny Cowley to play with three at the back at Adams Park. The News understands he's on the road to recovery and could be used against Stevenage to help get minutes under his belt ahead of the visit of MK Dons on Saturday. 60 minutes should do him tonight! Photo: Simon Davies
3. Michael Morrison - centre-back 1
With all of Danny Cowley's centre-backs fit, you can see Morrison getting the nod tonight. Simply because Sean Raggett and Clark Robertson are likely to start against the Dons on Saturday - barring injury, of course! Photo: Jason Brown
4. Sean Raggett - centre-back 2
Danny Cowley will unlikely want to make too many changes at the back as he looks to get the balance right in his team selection. With one eye on giving players much-needed game time and the other on wanting to win, Raggett's inclusion centres on the latter! Photo: Jason Brown