Pompey have been deprived of three left-sided players within a fortnight through injury.
Now Lloyd Isgrove is in the frame to plug the gap at Shrewsbury.
Viv Solomon-Otabor sustained a calf injury against Scunthorpe, while Dion Donohue was forced off with a groin problem for the reserves on Tuesday.
They join fellow wide-left player Ronan Curtis on the sidelines as the trio battle to be available for the Checkatrade Trophy final.
In the meantime, Kenny Jackett must identify an effective left-sided replacement for Saturday’s trip to Shrewsbury, which finally opens the door for Isgrove.
The Barnsley loanee has still to feature since his January switch, yet Jackett admits is now a starting XI option at New Meadow.
Alternatives include switching either Jamal Lowe or Gareth Evans onto the left flank.
Jackett said: ‘Isgrove could start against Shrewsbury.
‘He's worked hard and it has been frustrating for him because he hasn’t had much of a chance, but he knew what he was coming into and knew he would have to be patient.
‘Importantly, as well as being patient when the chances come, he has to take them.
‘If it works out for him now I’d be delighted, he’s a smashing lad, he has worked very hard and it will be interesting how it opens up for him now.
‘Isgrove is not left footed but mainly has played wide, he prefers that side, although can also play right.
‘If you asked him what his position was and where he is established, it’s right or left wing, he is an out-and-out winger.
‘As at every club, work hard to get the shirt and work harder to keep it.’
Following Solomon-Otabor’s withdrawal on the stroke of half-time against Scunthorpe, Evans came off the bench.
He operated on the right of the attacking three, with Lowe switching over the left.
And the pair also enter the equation for Saturday – along with Isgrove.
Jackett added: ‘For us, there are three options.
‘Gareth Evans, Jamal and Isgrove, it’s those three really.
‘Obviously Evans has played the majority of the season at number 10, but he has enough experience in the wide position.’