Last summer marked the end of an era for Tottenham Hotspur as homegrown midfielder Oliver Skipp brought his 16-year association with the club to a close.
The 24-year-old moved to Leicester City in a deal worth approximately £20 million, a transfer that continued a trend of business between the two clubs.
In recent years, Spurs and Leicester have been frequent trading partners. Harry Winks, another Spurs academy graduate, joined the Foxes for £10 million in the summer of 2023, while James Maddison headed in the opposite direction, signing for Tottenham in a £40 million deal during the same window.
Skipp Opens Up About Leaving Spurs
Speaking to The Athletic, Skipp reflected on his emotional decision to leave the club where he had spent his formative years.
“It was hard. It’s a club that’s been in my family and in my heart since I was young. My grandparents are all fans, and my parents. But as a player, you know when your time has come,” he said.
“I was grateful for the opportunities I got at Spurs and I made over 100 appearances that, as a boy growing up, was something you could only dream of. But there comes a time where you know the time is right and I felt this summer that it was the perfect opportunity to experience something else and to challenge myself. It was mixed emotions, but I was ready to move on.”
Skipp’s rise through the Tottenham ranks was marked by high expectations, particularly after his standout season on loan at Norwich City during their Championship-winning campaign in 2020/21.
The midfielder was pivotal in the Canaries’ success, starting 44 games and amassing 3,859 minutes.
While his Tottenham career didn’t unfold as some had hoped, Skipp still managed to make over 100 first-team appearances—an impressive milestone for any academy graduate.
His most memorable moment in a Spurs shirt was undoubtedly his stunning strike off the crossbar in a 2-0 victory over Chelsea in February 2023.
Since his move to Leicester, Skipp has faced challenges in securing a regular starting spot. He has started only five Premier League games this season and has often been an unused substitute.
The midfielder missed Leicester’s clash with Spurs in August due to the timing of his transfer, meaning his first opportunity to face his boyhood club will come in late January at the Tottenham Hotspur Stadium.
Despite moving on, Skipp remains a beloved figure among the Spurs faithful, with fans wishing him the best in his career at Leicester and beyond.
