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...
9. Michael Jacobs - left-wing
The popular attacking midfielder hasn't featured since picking up a hamstring injury at Charlton on October 17. Back fit, he now needs match minutes in his legs ahead of a busy fixture schedule over Christmas and New Year. Photo: Jason Brown
10. Dane Scarlett - centre-forward 1
Pompey seem to want to get as much game time out of the Spurs youngster as possible - and that's likely to continue against Stevenage. Photo: Jason Brown
11. Joe Pigott - centre-forward 2
If anyone needs more game time at present in the Pompey squad, it's the on-loan Ipswich striker. While others have had injury problems to fall back on, he's just been overlooked. With top-scorer Colby Bishop a must for MK Dons on Saturday, surely Pigott will get his chance to lead the line against the Boro? Photo: Jason Brown