“Harsh truth” issued over Conor Chaplin’s Portsmouth future – Ipswich Town contract decision looms

Conor Chaplin made an emotional return to Portsmouth on loan from Ipswich Town in the latter stages of the summer transfer window – but the move hasn’t exactly gone to plan.
Chaplin initially came through Pompey’s academy system over a decade ago, but he departed in 2018 for Coventry City.
Since then, he has gone on to play for Barnsley and the Tractor Boys, helping the latter gain promotion in back-to-back seasons from League One to the Premier League.
The 29-year-old made 22 appearances in the Premier League in 2024-25, scoring one goal, but he was loaned back to Fratton Park after a number of players arrived ahead of him over the course of a few transfer windows at Portman Road.
Many would have expected Chaplin to flourish back at his former home, but he’s not made much of an impact as Portsmouth look to try and stave off the threat of relegation to League One.
With the end of his loan spell on the horizon, a decision will need to be made soon regarding Chaplin’s long-term future, particularly as he is out of contract at Portman Road in June.
Portsmouth have greater priorities than Conor Chaplin’s future

When asked if the club should pursue a permanent contract for Chaplin, FLW’s Portsmouth fan pundit Miltos Ioannidis claimed that things just haven’t really worked out for the forward since returning to Fratton Park in the summer.
He believes that there is better value elsewhere in the transfer market, and that Pompey should focus their priorities on potentially tying down other loan players, and that only a strong run of form in the final months of the season could change that stance.
“The thing about Conor Chaplin is that things clearly haven’t worked out the way we all would’ve wanted,” Ioannidis told Football League World.
“Which is frustrating really because his return to the club came with huge excitement, and an enormous anticipation that he would be the same player that he was at Ipswich a couple of seasons ago, and had been for a number of seasons in the Championship.
“But things clearly haven’t worked out for him.
“I think the harsh truth is that there is better value elsewhere.
“We do have a couple of other loanees at the club right now that I think are way ahead in the pecking order, and I don’t know if they should accelerate the deal for Conor Chaplin.
“I think some transfers work out, some others don’t.
“This one had something extra in it with one of our own coming back to Fratton Park, but I wouldn’t really go over the edge and say he should make it permanent.
“Unless he gets himself in a ridiculous form in this last couple months, then I think this is not something that we should try and push through.”
Portsmouth are in their second season back in the Championship after gaining promotion from League One in 2024, and Pompey boss John Mousinho will be hoping Chaplin can turn around his form and aid their bid to stay in the second tier.