The NINE issues Danny Cowley must address to transform Portsmouth into promotion contenders ahead of Ipswich, Derby, Peterborough & Co

Like many others, Pompey enter pre-season looking to build the foundations of a promotion-pushing side and exorcise demons of their 10th-placed finish last term.

Danny Cowley will already be buoyed ahead of the Blues’ June 20 return as his wish for continuity is proving successful, with Sean Raggett and Reeco Hackett the latest to commit their futures to the club.

And with the transfer window opening in just over a week’s time, the Fratton chief will be hoping to strengthen his squad further.

But what areas require the manager’s attention most?

Here’s the nine conundrums he needs to tackle before the window slams shut on September 1

Contracts of attacking duo

Although Sean Raggett and Reeco Hackett have extended their stays, there is growing uncertainty over the futures of Aiden O’Brien and Michael Jacobs.

There is a desire from both to prolong their tenures, while the fans have made it clear they want to see them in royal blue next season as well.

Offers remain are on the table.

But if the club’s hierarchy haven’t offered what would be deemed satisfactory terms, they must sign players that will make the ex-Sunderland and Wigan forwards distant memories.

They will be opening themselves up to ridicule if they don’t.

Goalkeeping vacancy

It’s no secret Pompey need goalkeeping reinforcements following loanee Gavin Bazunu’s return to Manchester City.

At present, their only options are Alex Bass and Toby Steward.

The jury still out on the former, while the latter’s lack of experience makes him unsuitable to be heir to the throne.

Whoever is elected to take the Republic of Ireland international’s place will have big gloves to fill.

But it’s imperative they find the right man to execute Cowley’s preferred style of play.

Right-back competition

At present, Kieron Freeman and Haji Mnoga are the only options at right-back.

To some, this may seem as adequate competition, with an experienced campaigner challenged by an up-and-coming star.

But neither were trusted with the responsibility of the position last season.

Freeman was moved to centre-back as Mahlon Romeo dislodged him, while Mnoga was sent on two loans to gain first-team experience.

With this in mind, Cowley needs to decide if the duo are good enough.

Alternatively, he needs to invest in someone who is – whether that be Hayden Carter or someone else.

Cowley is keen to bring the Blackburn defender back to Fratton Park, following his successful loan spell.

However, the 22-year-old fancies his chances of cementing a place in the Championship instead.

Central midfield

With Shaun Williams departing at the end of his contract, Pompey will need to bolster their engine room options.

At present, Joe Morrell, Louis Thompson, Ryan Tunnicliffe and Jay Mingi are the only ones to pick from – but are the final two good enough over the course of a season?

Ex-Manchester United man Tunnicliffe started 2021-22 in great form but tailed off soon afterwards.

Meanwhile, supporters haven’t seen enough of the ex-Charlton man to judge.

The Pompey head coach has stated he requires a more defensive figure.

But just as important will be trusted fresh legs for what is guaranteed to be another tough, long season.

Strikers

There are currently no senior strikers contracted to the Fratton Park outfit – so it doesn’t take a genius to point out Cowley needs attacking reinforcements ASAP.

In fairness, he’s made it known that four new faces is his go-to figure in this department, while being specific about the qualities he wants from his front men.

Pace, power and athleticism top his wishlist – which is perhaps why it’s no surprise to see Kyle Wootton and Morgan Whittaker linked.

Regardless of who they sign, Pompey need to put the ‘curse’ of their strikers to bed.

Since their promotion to League One in 2017, 16 players have been tasked with firing the club back to the Championship – with all failing to date.

A No10

Across Cowley’s favoured 3-4-3 and 4-2-3-1 formations, a number 10 is imperative to each.

This means they need to finally find a trusted out-and-out player to perform the role.

For a number of years, players have been shoehorned into the position, resulting in an ineffective forward line.

Last summer, Scott Twine could have fit the bill, before his move to MK Dons.

If Jacobs isn’t the man, then they need to find someone of his quality or Twine’s to supplement the chosen striker.

Getting loan deals right

By last January, three of Pompey’s five initial loanees had failed to stamp their authority on the team – forcing a reshuffle at the turn of the year.

Miguel Azeez and Gassan Ahadme were replaced by Hayden Carter and Tyler Walker, before George Hirst put his underwhelming first half of the season behind him by netting 13 goals.

This time around, Pompey need to get it right at the first attempt, with Cowley searching for loanees who will be the cherry on the cake – not the mainstays of the team who will head back to their clubs at the end of the season.

Future of Harness and Curtis

After the out-of-contract contingent are dealt with, Cowley must swiftly and assertively address the futures of Marcus Harness and Ronan Curtis.

Admittedly, the former’s contract was extended – but this could easily be an exercise to protect their asset.

It feels the right time for the Fratton outfit to change up their wide men, too, after their productivity went slightly stale during the second half of last season.

Cowley revealed it would have to take the right price to take the ex-Burton man from his squad, but with Curtis’ contract expiring next summer, it could be the right time to cash in on both.

Inclusion of youth

A growing frustration that has increased year-on-year is the lack of academy progression into the first team.

This could be addressed next term, with Harry Jewitt-White, Steward and Dan Gifford penning new deals.

However, the players that are produced must earn the right to play competitively in the first team.

This is perhaps why the best avenue for them is by using the EFL Trophy as a springboard – but they need the chance to play in those matches.