From Portsmouth triallist to Sholing in two years, ex-Southampton Premier League starlet's latest south-coast destination

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He was trialling at Pompey two years ago – now the former Southampton midfielder has signed for Sholing.

Jake Hesketh has penned a deal with the Southern League Premier South newcomers following his release by Eastleigh.

It represents the next stage of the 27-year-old’s footballing journey after making two Premier League appearances until a St Mary’s release in the summer of 2021.

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That brought him to the attention of Danny Cowley, who ran the rule over Hesketh ahead of the 2021-22 campaign.

Having been appointed permanent head coach following an interim period, Cowley initiated a large-scale Fratton Park overhaul, albeit initially rendered well short of players for pre-season.

Hesketh was among a number of triallists to arrive, along with Ryan Leak, Corey Addai, Madger Gomes, Layton Ndukwu and Sam Habergham.

The likes of Jayden Reid and Jay Mingi impressed sufficiently to earn permanent stays, while Gassan Ahadme was secured on a season-long loan from Norwich.

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Still, Hesketh played in three Blues friendlies in the summer of 2021, while also attended their week-long training camp at St George’s Park.

The former Southampton midfielder Jake Hesketh trialled for Pompey in the summer of 2021. He has now joined Sholing. Picture: Chris Moorhouse.The former Southampton midfielder Jake Hesketh trialled for Pompey in the summer of 2021. He has now joined Sholing. Picture: Chris Moorhouse.
The former Southampton midfielder Jake Hesketh trialled for Pompey in the summer of 2021. He has now joined Sholing. Picture: Chris Moorhouse.

The former Burton, MK Dons and Lincoln loanee faced QPR in a behind-closed-doors fixture at their Imperial College training ground and then started a 5-2 victory over the Hawks.

At the end of the Blues’ stay at St George’s Park in July 2021, he appeared as a substitute in a 120-minute behind-closed-doors match against Burton.

However, following the culmination of that trip, Hesketh was released, with Cowley deciding the player wasn’t what he was looking for.

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The former Southampton apprentice went on to earn a deal at Eastleigh, featuring 54 times in two National League seasons, scoring twice.

Former Pompey triallist Jake Hesketh (right) has spent the last two seasons with Eastleigh. Picture: Mike Hewitt/Getty ImagesFormer Pompey triallist Jake Hesketh (right) has spent the last two seasons with Eastleigh. Picture: Mike Hewitt/Getty Images
Former Pompey triallist Jake Hesketh (right) has spent the last two seasons with Eastleigh. Picture: Mike Hewitt/Getty Images

Yet he was among six players released by boss Lee Bradbury at the end of a season which saw them finish an encouraging ninth in the table.

He has subsequently linked up with Sholing, who were promoted through the Southern League Division One South play-off final after beating Hamworthy United 2-0.

A club record crowd of 1,289 were in attendance for that occasion and the feel-good factor remains as they bid to face Southern League Premier South for the first time in the club’s history.

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That puts them in the same division as Gosport, with veteran boss Dave Diaper hoping Hesketh can be an influential figure.

Diaper told Sholing’s official website: ‘Jake is a very significant acquisition for the club and I thank all involved with making it happen.

‘He of course brings great quality, but also he adds a level of professionalism and experience which can only benefit the rest of the squad.

‘He'd fallen a little out of love for the game, but after watching our play-offs and spending some time at the club, he recognised what we have here is something special, with a team spirit like no other and he wanted to be a part of it.’