Ipswich Town have not started the season well at all, and after suffering relegation from the Premier League in 2024/25, it’s been tough to get back on track in the Championship.
The Tractor Boys left it late to take a point at home to Derby County on Saturday, with Jack Clarke scoring from the penalty spot deep into added time to ensure that Kieran McKenna’s side did not head into the international break on the back of a second defeat.
Nevertheless, the draw at Portman Road could potentially prove to be the final game in Suffolk for Conor Chaplin, with the versatile attacker moving back to Portsmouth on loan for the rest of the campaign.
It’s a decision that shocked Ipswich supporters, but there is the opportunity for the deal to play beautifully into the hands of the Tractor Boys almost straight away.
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Ipswich Town will hope that Conor Chaplin hits the ground running for Portsmouth
The last few days of the transfer window were busy ones for McKenna, with Luke Woolfenden just one of those leaving Portman Road.

However, Chaplin’s departure to Portsmouth will be particularly frustrating, especially as he is out of contract at the end of the season and could have played an important role at the club this season.
Yet, he returns to a team in Pompey who he adores and he will do everything he can to help push them to a mid-table finish, with the 28-year-old expected to make his debut immediately after the international break.
Portsmouth face Southampton at St. Mary’s, one of several derby games in the Championship this season, and if he can get off the mark against his new club’s bitter rivals, then that will only help Ipswich who are expected to be in the promotion fight in 2025/26.
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Conor Chaplin has unfinished business at Portsmouth
It’s been seven years since Chaplin left Pompey, as he made his way to Coventry City on loan before joining Barnsley at the start of the 2018/19 campaign on a permanent deal.
There is no doubting the forward has unfinished business on the south coast having left the club while they were in League One, and with the experience that he has gained in the time since he departed, he comes back a mature player.

His services would still have been welcome at Ipswich, but the game time he will get at Portsmouth perhaps made a return a no-brainer.
Now, he has the opportunity to make an instant impact that his parent club will want to see as Southampton are likely to be competing with the Tractor Boys at the top of the division this season.
