Conor Chaplin: Leicester 'plotting' free transfer move for former Portsmouth, Ipswich and Barnsley favourite
Conor Chaplin is on the lookout for a new club after spending last season back at Pompey on loan from Ipswich Town
Conor Chaplin’s next career stop could see him return to the Midlands.
Seven years after parting company with Coventry City for a move to Barnsley, the former Fratton favourite could be returning to the region with Leicester.
According to Football League World the forward, who spent last season on loan at Pompey from Ipswich Town, is on the Foxes’ radar as they plot an instant return to the Championship from League One.
The recently-relegated side will be rebuilding this summer ahead of their latest campaign in the third tier. That process has already seen former Southampton and Rangers boss Martin Russell installed as their new head coach.
Now attention is turning towards the players who will help them achieve their goal of a promotion-winning 2026-27 season, with Chaplin supposedly someone they believe will help them achieve their ambitions.
That’s understandable after the 29-year-old helped Ipswich secure their return to the Championship in 2023 as he netted 29 goals in all competitions that year.
The forward also notched 13 goals and recorded eight assists when helping the Tractor Boys reach the Premier League the following campaign.
And with the Portman Road side deciding not to trigger the 12-month contract option they had on the Worthing-born ace’s contract as they head back to the top flight, any move to the Kingspan would come free of charge.
Leicester will likely face competition for the former Pompey man’s services, though, with fellow League One side Oxford United also reported admirers of the attacking midfielder.
Chaplin Fratton return ruled out
A third stint at Fratton Park has already been ruled out for the Blues academy graduate, which frees up other clubs to pursue the player.
Speaking last month to BBC Radio Solent, Pompey sporting director Rich Hughes said other targets were on their radar after Chaplin competed the 2025-26 season with two goals and three assists from 37 Blues games.
When asked if Chaplin would return to Fratton Park next season, Hughes said: ‘At this point I would probably say no.
‘We're really grateful for Conor's impact around the group last year. I think Conor would probably be the first one to say it probably wasn't the return he hoped for, but what he was was an unbelievable character around the building and he was a leader, which I think speaks testament to Conor as a person and as a natural leader.
‘To come in as a loan player and show that level of commitment to a group in terms of how he developed it, how he worked with the younger players, how he trained consistently every day, and how he sort of engaged with everything that we ask of players in this football club is testament to him.
‘But it's not something that we pursued at the minute and not something we're really actively looking to bring in.
‘But I think anyone that spoke to anyone who's affiliated with this football club would tell you what an unbelievable person and character Conor is.
‘We've also sought his feedback on what he saw, what he thought and how we can get better as a group as well.’