Conor Chaplin has chosen five former Portsmouth players to re-sign with Danny Cowley

Conor Chaplin has chosen five former Portsmouth players to re-sign with Danny Cowley ...

Portsmouth are set to sell Alex Bass and Kieron Freeman to raise money for the club. Danny Cowley should use the money to re-sign a number of former Pompey players to build a promotion-worthy side.

The Fratton Park natives finished their lowest league performance since winning the League Two championship in 2016/17 last season. Cowley could only manage the south coast side to tenth-place in his first full season in charge of the League One team since replacing Kenny Jackett in 2021.

Portsmouth's play-off football remained out of reach for a fourth season thanks to a drop down the standings. Jackett had led Pompey to the post-season during the 2018/19 and 2019/20 seasons, but he could not avoid losing at the semi-final stage on both occasions.

Cowley should utilize Bass and Freeman funds to re-sign current Portsmouth players.

Cowley has agreed to a few transfers as he restructures his Pompey team this summer. Marlon Pack, Joe Rafferty, Joshua Oluwayemi, and Zak Swanson have agreed to permanent moves to the south coast, while Josh Griffiths and Joe Pigott have arrived on loan.

The Portsmouth manager expects to make additional changes before lifting the League One curtain on July 30 at Sheffield Wednesday. The Fratton Park hierarchy will allow Cowley to reinvest the funds from the anticipated sales of Bass and Freeman following Marcus Harness.

Bass and Freeman are currently in discussions with possible sides about permanent moves, according to reports from The News. Burton Albion, Hull City, Mansfield, Swindon Town, and Tranmere Rovers are all interested in Bass and Freeman.

According to The News, Cowley is interested in returning George Hirst to Fratton Park following his loan from Leicester City last season. But Portsmouth are worried about losing out on the 23-year-old on a big-money move or Championship loan, while Ipswich Town have also applied.

Which other former Portsmouth players should Cowley consider re-signing to help strengthen a side he expects to lift himself up?

Conor Chaplin of Ipswich Town should be re-signed by Portsmouth.

Conor Chaplin, a former Portsmouth player, may be re-signed by Cowley. The 25-year-old striker currently plays for League One side Ipswich, having moved to Portman Road from Barnsley last year.

Ipswich are the Chaplins' third team since he left the club in January 2019. He played 122 senior matches for the Blues across all competitions, scoring 25 goals and seven assists. The Worthing native would go on to score 17 in 86 for Barnsley.

Chaplins' first campaign at Portman Road resulted in the 5 foot 6 forward scoring 11 goals in 47 league matches. He also provided three assists in 39 League One appearances, while also providing a versatile attacking option with minutes on both wings and in several central roles.

Portsmouth should sign former Mansfield Town player Oliver Hawkins.

Cowley, a former Portsmouth player, should consider re-signing, according to Oliver Hawkins of Mansfield. The 30-year-old can offer the Fratton Park club an interesting, versatile option with a return to the south coast, having excelled as a centre-forward and centre-back.

Hawkins made 41 starts in League Two last season, scoring seven goals and an assist. Yet only 12 of his starting goals came from a striker, while he found the net a further three times in 27 games as a central defender.

While on the south coast, the London-born player showed his surprising versatility. Between 2017 and 2020, Hawkins made 55 starts from striker and opened 16 matches from centre-back.

After an injury nightmare, Danny Cowley should offer Matty Kennedy regular games.

After the forwards' horrific year with injuries last season, Cowley should offer former Portsmouth loanee Matty Kennedy regular game time. The 27-year-old started only three games across all competitions.

Following a grueling summer of fitness training, Kennedy made all of his outings for the term at the start of the year. But the Aberdeen winger is now pain-free and looking to restore his former form.

In his first season as a three-cap Northern Ireland international, Kennedy accumulated six assists and a goal over 35 games in 2020/21. He has also started the new season strong with two goals and an assist in three Scottish League Cup games.

Connor Ronan's return to Fratton Park would be worthwhile, but Portsmouth will have to wait to see him.

Connor Ronan might be worth Cowley's consideration of re-signing, but Portsmouth will have to wait for Wolves to make their final decision. Bruno Lage will give the midfielder a chance to impress in pre-season before the Molineux manager makes any changes.

After his successful loan spell at St Mirren last season, Lage wants to see how Ronan reacts to his old club. He scored eight goals and five assists, including striking seven goals and establishing another four more in his 25 Premiership appearances.

Despite Hearts and Aberdeen's interest, Wolves remain open to selling Ronan. However, Ronan would be a welcome addition to Fratton Park if Portsmouth re-signs their 2018 loan player, who played 16 games in League One for the Blues.

Portsmouth should look to sign Charlton Athletic's Jayden Stockley.

Cowley will have to use the money raised by selling Bass and Freeman to buy a striker. A former Pompey player can answer his calls for Jayden Stockley, who scored 13 League One goals (all comps) for Charlton Athletic last season.

The Blues should at least make an enquiry. According to The Star, Owls boss Darren Moore has cooled his interest in signing Michael Smith.

Moore is a big supporter of Stockley and appreciated his physical presence when considering a different forward position. The Poole-born attackers' development since his loan spell with Pompey in 2015 would also see Stockley offer far more than he did in that season, with two goals in 12.

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