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Conor Chaplin among 5 former Portsmouth players Danny Cowley should now re-sign

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Portsmouth are set to sell Alex Bass and Kieron Freeman, raising funds boss Danny Cowley should use to re-sign a clutch of former Pompey players to build a promotion-worthy side.

The Fratton Park natives produced their lowest league finish since winning the League Two title in 2016/17 last campaign. Cowley could only lead the south coast side to 10th-place in his first full season in charge of the League One team after replacing Kenny Jackett in 2021.

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

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Cowley should use Bass and Freeman funds to re-sign former Portsmouth players

Cowley has so far agreed a handful of transfers as he strives to reshape his Pompey squad 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 arrived on loan.

But the Portsmouth boss expects to make further additions before raising the League One curtain at Sheffield Wednesday on July 30. The Fratton Park hierarchy will allow Cowley to reinvest the funds of the anticipated sales of Bass and Freeman to follow Marcus Harness.

Reports by The News note Bass and Freeman are currently in talks with possible sides over permanent moves. Crawley Town and Exeter City are interested in Bass, while Freeman is on the radars of Burton Albion, Hull City, Mansfield, Swindon Town and Tranmere Rovers.

Cowley is interested in taking George Hirst back to Fratton Park following the striker’s loan from Leicester City last season, per The News. But Portsmouth now fear missing out on the 23-year-old to a big-money move or Championship loan, while Ipswich Town have also bid.

So, with Hirst unlikely to return to the south coast, which other former Portsmouth players should Cowley now consider re-signing to strengthen a side he hopes can seal promotion?

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Portsmouth should look to re-sign former player Conor Chaplin of Ipswich Town

One former Portsmouth player Cowley should look to re-sign is Conor Chaplin. Although a deal for the 25-year-old to return to Fratton Park would be tough to agree with the striker now at League One rivals Ipswich, having moved to Portman Road from Barnsley last year.

Ipswich are Chaplin’s third side since the Pompey academy product left the club in January 2019. He departed following 122 senior games for the Blues across all competitions for 25 goals and seven assists. The Worthing native would go on to score 17 in 86 with Barnsley.

Chaplin’s first campaign at Portman Road resulted in the 5 ft 6 forward finding the net 11 times over 47 games. He also laid on three assists over 39 League One appearances, while giving a versatile attacking option with minutes on both wings and in several central roles.

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Portsmouth should look to re-sign former player Oliver Hawkins of Mansfield Town

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

Hawkins made 41 appearances in League Two last term and started 39 games for seven goals and one assist. Yet just 12 of his starting calls came from striker for four goals and the assist, while finding the net a further three times in 27 games as a central defender.

The London-born star demonstrated his surprise versatility whilst on the south coast, as well. Of his 96 appearances for 18 goals and nine assists with Portsmouth, Hawkins made 55 starts from striker and opened 16 matches from centre-back between 2017 and 2020.

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Danny Cowley should offer Matty Kennedy regular games after injury nightmare

Cowley should look to offer former Portsmouth loanee Matty Kennedy regular game time in the upcoming season after the forward’s nightmare year with injuries last term. The 27-year-old only managed to play nine times and started three games across all competitions.

Kennedy made all of his outings for the term following the turn of the year after sustaining two stress fractures in his back last summer. But the Aberdeen winger is now pain-free and looking to recapture his past form following a gruelling non-stop summer of fitness work.

The three-cap Northern Ireland international recorded six assists and a goal over 35 games in 2020/21. And he has started the new season strongly with two goals and an assist across three Scottish League Cup ties. So, Kennedy will be eager to maintain his early momentum.

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Connor Ronan would be worth Fratton Park return but Portsmouth face waiting

Connor Ronan would be worth Cowley considering re-signing, but Portsmouth face waiting for Wolves to make their final decision. The Express & Star note Bruno Lage will afford the midfielder a chance to impress in pre-season before the Molineux boss deliberates moves.

Lage wants to see how Ronan reacts back with the Premier League side after his successful loan spell at St Mirren last season. The 24-year-old offered eight goals and five assists over 30 games, including striking seven and creating a further four over 25 Premiership outings.

Wolves remain open to selling Ronan, nonetheless, with Hearts and Aberdeen registering their interest. But Ronan would be a welcome addition at Fratton Park if Portsmouth were to re-sign their 2018 loan player, who made 16 appearances in League One with the Blues.

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Portsmouth should look to re-sign Jayden Stockley of Charlton Athletic

Cowley will have to use the funds that Portsmouth raise through selling Bass and Freeman to sign a striker. And a former Pompey player can answer his calls in Jayden Stockley, after the 28-year-old hit 13 League One goals (20 in all comps) for Charlton Athletic last season.

It will take a lot to prise the forward from the Addicks, but the Blues should at least lodge an enquiry. Any pursuit is also unlikely to face competition from Sheffield Wednesday, as The Star report Owls boss Darren Moore has cooled his interest after signing Michael Smith.

Moore is a big fan of Stockley and appreciated his physical presence when targeting a new forward option. The Poole-born attacker’s growth since his loan spell with Pompey in 2015 would also see Stockley offer far more than he managed that season with two goals in 12.
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