With just two matches of the League One season remaining, the Blues can’t afford any margin for error if they’re to clinch a League One play-off spot.
Pompey are sixth in the table but need eighth-placed Charlton, who have a game in hand, to also drop points.
It makes for an exciting end to the campaign as Danny Cowley bids to guide the Blues to promotion having only taken the hot seat in March.
Pompey’s injuries problems are well-documented, with the likes of Ellis Harrison and Michael Jacobs on the sidelined.
Then there are players such as Tom Naylor and Andy Cannon battling through the pain barrier to try to deliver a Championship return.
Here’s how we think the Blues will start for their first trip to Wimbledon’s Plough Lane...
5. Left-back - Lee Brown
Will he finally be back?! Certainly it will give Pompey a huge boost if Brown is fit to start. Photo: Joe Pepler
6. Centre-midfield - Tom Naylor
Currently playing through a hamstring injury in Pompey's bid for promotion. Photo: Joe Pepler
7. Centre-midfield - Ben Close
Was withdrawn at half-time at Accrington but been a key player since the Cowleys' arrival. Photo: Joe Pepler
8. Right-wing - Marcus Harness
Started brightly at Accrington before fading and could do with a goal or assist to boost confidence again. Photo: Daniel Chesterton