Barnsley backed to seal Conor Chaplin transfer | OneFootball

FLW's Barnsley fan pundit would love to see Conor Chaplin back at Oakwell, but can see some stumbling blocks in a race to bring him in

The destination of Conor Chaplin after departing Ipswich Town this summer is one of the more intriguing free agent stories of the 2026 offseason.

The 29-year-old spent the 2025/26 campaign on loan at Portsmouth, the club he began his career at, but had a massively disappointing season when taking into consideration how integral he was to Kieran McKenna's promotion-winning side two years ago.

Understandably, two goals and three assists in 36 league games at Fratton Park didn't do enough to warrant a contract extension at Portman Road as Ipswich gear up for a Premier League return, but would it do enough to see a fellow Championship side offer Chaplin fresh terms?

If he were to find his future lying in League One, a reunion with Daniel Stendel at Barnsley could be on the cards. Chaplin was brought to Oakwell by the German boss seven years ago, but he was then sacked just two months later as they struggled in the Championship.

Nevertheless, with Stendel making his return to the Tykes this summer, the fact that this Barnsley side needs attacking reinforcements, and the fact that Chaplin netted a season-high 26 goals the last time he was in the third tier, he could seem to be the perfect summer signing.

Barnsley return for Conor Chaplin would be welcomed despite past Tykes comments

Despite Chaplin's form being a bit of a concern in the past couple of years, as he struggled to get into the Ipswich side in the Premier League and failed to rediscover his scoring touch at Portsmouth, FLW's Barnsley fan pundit, Andy Symcox, would still welcome him at Oakwell.

The 29-year-old thrived in Kieran McKenna's free-flowing attacking system as they bounced up from the third tier to the top flight, and the fan pundit believes that Daniel Stendel's system could mirror that next season.

"I personally would be very happy for Conor Chaplin to return to Oakwell," Symcox told FLW. "There is no doubt in the new season under Daniel Stendel that we need a striker.

"Conor's style of play would suit Stendel's approach, attacking football with a high press, and he did that with great aplomb when Daniel signed him seven years ago."

However, with Chaplin coming off the back of a contract that saw him play in the Premier League, the fan pundit isn't too convinced that Barnsley - who haven't exactly been handing out lucrative contracts on the regular recently - would be able to afford his wages.

That's not all, either, as the 29-year-old was rather outspoken about the then-board at Oakwell during his time at the club, questioning their ambition to win football games and stating that he felt that the fans were "let down a lot of the time by the board and the hierarchy".

But, there have been changes to that board since the Tykes returned to League One in 2022, with the majority of the consortium who took over the club in 2017 departing. Symcox hopes that this could open the door for a possible Chaplin return.

"I can't see that we would pay the wages required to secure his services, and I think that it's fair to say that, when Conor left, he left under difficult circumstances, and he said some things about the club that, while probably very true, isn't something you'd say if you were planning on returning," Andy admitted.

"Having said that, he was talking about a previous CEO and owner who were ultimately replaced by the current board, so never say never.

"I would welcome him back with open arms as he is the type of player that will suit the style of play that I hope Stendel will adopt this coming season."

Daniel Stendel's appointment may provide the assurance needed for Conor Chaplin to return to Barnsley

While Chaplin's comments after leaving Barnsley may have been taken negatively, there is no denying that, factually, the Tykes have gotten worse in each of the past six years, finishing lower and lower each season following their Championship play-off appearance in 2021.

Therefore, the re-appointment of Stendel has gotten some Barnsley fans excited, as this could be an indication that the club are serious about getting back into the second tier.

The 52-year-old led the club to their record points tally, finishing the 2018/19 League One campaign with 91 points, went unbeaten at home throughout the season and only conceded 39 times, and if he can replicate any of that in 2026/27, it'll be much appreciated at Oakwell.

Granted, there's still a lot of work to do with the squad currently. Seven years ago, that team had the likes of Liam Lindsay, Ethan Pinnock, Brad Potts, and Kieffer Moore in it, just to name a few, and the squad at present doesn't have nearly as much quality in it.