The play-off race will boil down to the wire, with the Blues' trip to AFC Wimbledon very much must-win if they're to achieve their ambition of promotion.
And away from Fratton Park, the Blues' two loanees also have two crucial games remaining - but for starkly contrasting reasons.
Reeco Hackett-Fairchild and Bryn Morris are both hoping they avoid maiden relegations on their CVs at Southend and Northampton respectively.
The drop looms large for both outfits and their fates could be confirmed come 5pm tomorrow.
Hackett-Fairchild's Southend are already virtually down and look set to lose their Football League status.
The forward moved to Roots Hall in January in a bid to help the Shrimpers retain their League Two status, having impressed at Bromley during the first half of the season.
However, despite bringing back Phil Brown to take over from Mark Molesley in the hot seat, the Essex outfit are six points adrift with two games remaining.
Not only do the Shrimpers must win their remaining two games – against Barrow and Newport – but have to hope Scunthorpe lose their final two matches and there’s a goal difference swing of nine.
Should Southend someone stay up, it'll be nothing short of a footballing miracle.
Morris has a better chance of League One survival at Northampton, although it's still going to be tall order.
The midfielder fell well out of favour at Pompey under former boss Kenny Jackett, who allowed him to join the Cobblers in January.
Morris has played 20 times at Sixfields and having started the past nine games, he's going to be a crucial player in Jon Brady's side's remaining two fixtures.
Northampton are one of four teams who can still go down to the fourth tier, along with Rochdale, Wigan and AFC Wimbledon. Bristol Rovers and Swindon have already gone down.
The Cobblers are four points from safety but have two tough fixtures remaining against promotion-chasing Blackpool and Sunderland.
Should Wigan defeat either Hull or Swindon, that will consign Northampton immediately back to League Two, while they need Wimbledon to lose both games and ensure there's a goal difference swing of 10.
It had been thought Morris had played his final game for Pompey when he moved to Sixfields due to his contract expiring in June, having been surplus to requirements under Jackett.
However, new head coach Danny Cowley has admitted he's being open-minded when it comes to the former Middlesbrough man's future.