Conor Chaplin returned to Portsmouth last summer on loan from Ipswich Town.

The playmaker progressed through Pompey’s academy system before joining Coventry City in 2018.

He helped the Tractor Boys win back-to-back promotions in 2023 and 2024, but he was loaned out following their relegation to the Championship in 2025.

However, Chaplin’s return to Fratton Park did not go as planned, with the 29-year-old scoring two goals and providing three assists in 36 league games.

His future is now uncertain, as his contract with Ipswich will expire this summer, leaving him a free agent.

Portsmouth could pursue a permanent deal for Chaplin, with FLW reporting exclusively that Derby County is also interested in signing him.

Portsmouth Update on Conor Chaplin’s Future

Portsmouth sporting director Richard Hughes has stated that Chaplin is unlikely to sign for the club on a permanent basis following his loan spell from Ipswich.

He feels the playmaker would be the first to acknowledge that his return to Fratton Park did not go as planned, even if he maintained a positive attitude, and that they are not actively pursuing a trade at this time.

“At this point, I would probably say no,” Hughes told the BBC.

“We are appreciative for Conor’s impact on the group last year.

“I think Conor would be the first to admit that it wasn’t the return he hoped for, but he was an incredible character around the building and a leader, which I believe speaks to Conor as a person and a natural leader.

“To come in as a loan player and demonstrate that degree of devotion to a group in terms of how he built it, how he worked with the younger players, how he trained regularly every day, and how he engaged with everything that we want of players in this football club is a compliment to him.

“But it is not something we are now pursuing or actively looking to bring in.

“But I believe anyone who speaks with anyone associated with this football club would tell you what an incredible 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.”

Supporters welcomed Chaplin’s return to Portsmouth, hoping he could assist the squad improve on their 17th-place performance in 2024/25.

However, in their second season back in the Championship, the squad dropped to 18th place under John Mousinho.

However, Hampshire improved their overall point total and escaped relegation by eight points, ending comfortably ahead of the bottom three.

The 29-year-old’s future is uncertain, as his contract with Ipswich expires later this month, leaving him a free agent.

Portsmouth’s decision not to pursue a permanent move will allow Derby to potentially secure his signature.

Chaplin previously helped Ipswich achieve promotion to the Premier League by scoring 13 goals and providing eight assists in 44 games in 2023/24, as Kieran McKenna’s team finished second in the table.

The Rams finished seventh this season, missing out on a play-off spot by four points, and John Eustace is now looking to strengthen his side.

Derby will hope for another top-eight finish next season, as the play-offs grow to include two more teams in 2027.

Derby get a free go at Conor Chaplin.

Derby may have a free run at Chaplin now that Portsmouth has withdrawn from the race to recruit him.

While he struggled with Mousinho’s team this year, his previous record suggests that he might return to his best in the proper atmosphere.

Given that he will also be a free agent, this is a pretty low-risk deal, with the only big financial concern being his salary.

Derby have previously handled the free agent market well, with Rhian Brewster joining last season being a prime example, so this is a deal with some promise, even if there are some caution signs following his dismal stay at Fratton Park.