Former Portsmouth and Ipswich Town favourite enduring Leicester City frustrations after summer switch
Conor Chaplin joined Leicester City in the summer after his Pompey loan stay came to a close.
Conor Chaplin has endured a frustrating start to his Leicester City career.
The 29-year-old, of course, arrived at the King Power Stadium on a free transfer after Ipswich Town opted against extending his five-year Portman Road stay.
It followed an underwhelming homecoming with Pompey, where he struggled to hit the heights many expected during his season-long loan.
While it’s been a far from ideal start to the season for Russell Martin’s side, who sit 16th in League One, the attacker himself has been heavily impacted by injury in the opening weeks of the season.
Leicester City frustrations for ex-Pompey & Ipswich favourite
Having missed much of pre-season as well as the opening two matches of the campaign due to a minor knock, the Fratton Park academy graduate returned from the sidelines to face former club Ipswich in the Carabao Cup and started a league outing against MK Dons.
But Chaplin suffered a recurrence of the injury issue during the goalless draw at Stadium MK and subsequently sat out the final four matches before the international break.
Martin, who remains under fire following a disappointing start to the season, has revealed the Foxes have had to resist temptation to fast-track the ex-Pompey man’s return.
Speaking to BBC Radio Leicestershire, the head coach said: ‘He’ll be in a good place after the international break. I think we’ll utilise this time.
‘Of course, there’s always the temptation to bring him back in quickly but we’ve just got to be patient.
‘I think the international break will be good for him because it gives him some more training time and then he’ll be back after that.’
Conor Chaplin’s Pompey career
Chaplin, of course, rose through the ranks at Fratton Park and went on to amass 122 appearances during his first stint on the south coast, where he collected 37 goal contributions.
After spells with Coventry, Barnsley and Ipswich, the attacking midfielder returned to his boyhood club in September 2025 on a season-long deal from the Tractor Boys.
Excitement greeted the 29-year-old’s capture at the end of last summer’s transfer window, but the academy graduate’s return wasn’t the anticipated success story - as he scored two goals from 37 appearances.
Following the end of his loan agreement, the Blues opted against signing Chaplin on a permanent basis having been released by Ipswich after the season’s climax.
And speaking in the summer window, sporting director Rich Hughes confirmed it was a deal Pompey were not looking to pursue.
He said in June: ‘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.’