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...
13. Sub 3 - Paul Downing
Made his first league outing since September 2019 at Accrington. Interesting to see what happens with his Pompey career now. Photo: Graham Hunt
14. Sub 4 - Charlie Daniels
Found himself on the bench in the past two games. Photo: PinPeP
15. Sub 5 - Harvey White
Highly regarded by the Cowleys but they need proven League One performers in the engine room for the final two games. Photo: Dennis Goodwin
16. Sub 6 - Andy Cannon
Played 45 minutes at Accrington but still evidently struggling with a back problem. Photo: Joe Pepler