James Bolton is likely to make his comeback in the Leasing.com Trophy on Tuesday night.
Pompey begin their defence of the silverware won at Wembley back in March when they host Crawley in a Southern Group B fixture.
An ankle problem has restricted the right-back to just 37 minutes of competitive action since his summer switch from Shrewsbury.
Blues boss Kenny Jackett said: “James and Sean (Raggett) have both had disrupted pre-seasons and need the games.
"It’s a good chance for James to play for us and get to the level of form that we know he’s capable of producing."
“We’ve got this one and then also Doncaster in the Premier League Cup the following week, which is useful.
“It’s a good chance for James to play for us and get to the level of form that we know he’s capable of producing.”
Oli Hawkins and Ryan Williams have both returned to training, but are unlikely to start against Crawley.
Meanwhile, Bryn Morris is set to see a specialist in Ireland about an ongoing stomach problem that has seen him sidelined for the start of the season.