Permanent signings may prove a challenge should the Blues fail to offload their high-end earners.
Nevertheless, we’ve taken a look at five realistic signings Pompey could make in the month ahead.
The Notts County striker has been heavily linked with Pompey going into the January window and it seems the Blues could very well pull off a move for the 25-year-old.
A prolific goalscorer in the National League, Wootton has scored 12 goals in all competitions this season and would represent a good and affordable solution to the Blues’ attacking issues.
Any deal would most likely depend on the departure of either John Marquis or Ellis Harrison.
Nevertheless, Wootton’s County contract expires at the end of the season, which opens the door to a cut price deal in January.
It would prove a mouthwatering attacking line-up – alongside Marcus Harness, Ronan Curtis and George Hirst – should Pompey complete signing of Wootton.
The Cheltenham centre-back has been linked with Pompey over recent weeks and, alongside Wootton, looks a signing that could realistically be struck in January.
It’s been reported that the Robins would be willing to let their captain depart for a six-figure fee, with his contract set to expire in the summer.
That’s not something the Blues will be keen to do given the fact that Boyle will be available on a free in six months.
So some sort of compromise will be required to make it happen – something that could materialise the longer the window progresses.
That would present a statement of intent from Danny Cowley, with Boyle linked with Sheffield Wednesday and Oxford in the summer.
However, just like Wootton, any deal could depend on the departure of high-earner Paul Downing, who has been linked with a return to Doncaster Rovers.
The midfielder is out of contract at Millwall at the end of the season – and currently out of favour at The Den – which could open the door to a cut price deal next month or a free transfer in the summer.
A player who is loved by Pompey fans, a return would go down well among the Fratton faithful.
One sticking point could be the current make-up of the Blues midfield.
Danny Cowley is well stocked in that area, boosting players of the calibre of Joe Morrell, Shaun Williams, Ryan Tunnicliffe, Louis Thompson and Miguel Azeez. Thompson’s wages would be a stumbling block, too.
However, Azeez’s Fratton future remains in doubt.
Meanwhile, with Sean Williams and Louis Thompson currently on one-year deals, could a summer move – when the Blues will have more money at their disposal – end years of transfer speculation?
The Aston Villa forward has spent the first half of the season on loan at Ipswich but has failed to get regular game time at Portman Road.
In his short career, the youngster has trained with Lionel Messi at Barcelona, spending six months at the Camp Nou aged 16.
But after limited game time in the Barca academy he joined Villa for £3m in January 2020.
The 18-year-old has made just two appearances in League One this season and reports suggest Villa will pull the plug on his Tractor Boys loan next month.
It is also suggested that the Villains are willing to let the striker go out on loan to another League One club in January in a bid to kick-start his development.
Barry is mostly remembered for his goal for Villa against Liverpool in last season’s FA Cup.
He clearly knows where the back of the net is, is a hot prospect for the future and it would be worth Cowley taking a gamble on the former Barcelona man.
The striker has played twice for Arsenal’s first team this season and has been tipped for a loan move away from the Emirates next month.
The 20-year-old scored twice for the Gunners’ under-21s side in this season’s EFL Trophy.
Meanwhile, 14 goals have been recorded for Arsenal under-23s side in Premier League 2,
There’s interest in Balogun from the Championship, so if Cowley could lure him to Fratton Park it would represent something of a coup.
The Blues boss has built a good relationship with the Gunners, with Miguel Azeez’s move to the south coast in the summer proof of that.
A message from the Editor, Mark Waldron
You can support our local team of expert Pompey writers by subscribing here for all the latest news from Fratton Park for 14p a day.