Oliver Skipp: where is he now?

From Tottenham mainstay to a £20m move

Oliver Skipp's rise through Tottenham's youth ranks felt like a model of patient development. After progressing through Bengeo Tigers and then the Spurs academy from the age of eight, he made his senior bow in a League Cup win over West Ham in October 2018 and gradually worked his way into first-team contention. A loan spell at Norwich City in 2020-21 proved pivotal: he helped the Canaries win the Championship title and was named in the PFA Team of the Year, evidence that his reading of the game and ball-winning instincts translated well outside Tottenham's system.

Back at Spurs, Skipp established himself as a regular in the 2021-22 campaign before a pelvic injury curtailed his season. He fought back to fitness, signed a new long-term contract, and even found the net in a north London derby moment of his own, opening the scoring against Chelsea in February 2023. He also tasted international success that summer, coming off the bench as England's Under-21s beat Spain to lift the European Championship.

Despite all that progress, Skipp's path at Tottenham eventually led elsewhere. In August 2024, Leicester City paid £20 million to bring him to the King Power Stadium on a five-year deal, and he made his debut off the bench in a defeat to Fulham.

Where he is now

Leicester's slide out of the Premier League has since taken Skipp with them, and now, two years into his Leicester contract, he finds himself out on loan again. On 1 September 2026, Skipp joined Championship side Charlton Athletic for a season-long loan spell, a reminder that although his parent club now sits in League One, there remains an appetite from Championship sides to take on a player of his pedigree and ball-winning qualities.

It is a notably different stage to the one he once occupied at Tottenham and in an England shirt, but the qualities that made him stand out as a teenager, his composure under pressure and his ability to break up opposition attacks, are presumably exactly what Charlton hope he can bring to their promotion push this season.

A career built on substance over style

Skipp was never the most eye-catching player to watch, but those inside the game recognised his worth early. Grant Hanley, his Norwich teammate during that loan spell, once remarked that Skipp possessed an experience beyond his years, praising his game intelligence and decision-making. That assessment has largely held up: a Championship title, a European Under-21 crown, and a £20 million valuation from Leicester all speak to a player whose contribution was always felt more than it was celebrated.

Whether this Charlton loan becomes a stepping stone back towards regular first-team football at a higher level, or simply another chapter in a career that has taken more unexpected turns than once seemed likely, remains to be seen. For now, fans who remember the composed young midfielder breaking into Tottenham's side will find him doing a similar job in SE7, trying to help Charlton climb the Championship table.