South London Sport: Charlton Athletic Edition

South London Sport: Charlton Athletic Edition

Why has it not worked out for Oliver Skipp at Leicester City? Midfielder, who commanded £20million fee two years ago, discusses being handed another Championship chance at Charlton Athletic

Addicks boss Jones explains reasoning behind bringing in former Tottenham man

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Rich Cawley
Sep 09, 2026
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“I had conversations with the people here and they gave me a feeling of warmth and comfort. I’m looking to push on.”

That was one of the comments made by Oliver Skipp not long after the ink had just dried on his Leicester City contract in August 2024.

There isn’t a lot of warmth or comfort when it comes to the Foxes now. Back-to-back relegations from the Premier League to League One have soured the mood to the point of serious pollution.

So why did it go awry for Charlton Athletic’s new loan signing in the East Midlands following that £20million transfer from Tottenham?

“I believe Skippy offers us another really calming influence in midfield that can support our game well,” said then Leicester manager Steve Cooper. “It’s great that he is here.”

But Cooper, who worked with Skipp while England boss at U17 and U18 level, was sacked just 12 matches into that Premier League season.

Skipp played 79 minutes in a 2-1 loss to Chelsea on November 23, which proved to be the tipping point for Leicester’s hierarchy to end Cooper’s employment. He had been an unused substitute for the three matches prior to that.

“The main reason it didn’t work out is that he never had a set role in a Leicester team,” said Josh Holland, who covers the Foxes for the Leicester Mercury. “He worked under so many managers in such a diabolical period for the club. He suffered two relegations.

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