Yet a potential return to Fratton Park this season is regarded as a bonus rather than confident expectation.
The left-back damaged his left knee only 39 minutes into the campaign and subsequently underwent an operation.
At the time it was anticipated the Huddersfield man would be unable to play again this season during his recovery.
However, as his comeback gathers pace, there remains a glimmer of hope that Holmes-Dennis could be back in action in April.
Although whether a training return from a long-term injury warrants an instant recall is open to debate.
Still, Blues boss Kenny Jackett has not ruled out the possibility of seeing the 22-year-old back at Fratton Park, no matter how unlikely it appears.
Holmes-Dennis has been receiving treatment with parent club Huddersfield ever since his knee operation and, by all accounts, is progressing well.
Pompey are, of course, still making a contribution towards the full-back’s wages, regardless of his long-time unavailability.
In accordance with the terms of the season-long loan, Holmes-Dennis is effectively still a Blues player until the deal expires or is cancelled.
Jackett also suffered injury misfortune with the replacement – Damien McCrory.
He damaged his knee against Fleetwood in September during a third appearance for the club.
The Burton left-back’s loan is scheduled to expire next month and the chances of him playing for Pompey again appear bleak.
Jackett also plans to recruit a left-back in January.