Oliver Skipp speaks on exit from Spurs | OneFootball

Last summer, homegrown and club trained midfielder Oliver Skipp ended his 16-year association with Tottenham Hotspur, as he joined Leicester City on a permanent transfer, for a fee of around £20 million pounds.

Business between the two clubs has not been uncommon in recent times, with fellow academy graduate Harry Winks also joining the Foxes on a permanent transfer, for around £10 million in the summer of 2023. That same window, James Maddison came the other way, joining Spurs for around £40 million pounds.

Former midfielder speaks on his exit from Tottenham Hotspur

In a recent interview with the Athletic, Skipp has spoken about leaving N17 after so long at the club. The 24-year old said: “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.

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."

There had been a lot of promise around Skipp, after a really fruitful season long loan with Norwich City in the Championship, where he started 44 games and 3859 minutes as they won the league in the 20/21 season.

Whilst it didn’t quite work out like the player or club would have hoped for, not many academy players have over 100 first team appearances to their name. The highlight of his Spurs career was no doubt his excellent finish off the bar, in a 2-0 win over Chelsea back in February of 2023.

So far this season, the 24-year old has started only five of Leicester's Premier League games, often finding himself as an unused sub. The midfielder was still finalising his transfer to the Midlands when his current side faced Spurs in August, so his first chance to play against the club will be in late January, when the two sides meet at the Tottenham Hotspur Stadium.

Other than that game, you can be pretty confident that the whole of the fanbase wishes him well this season and in all of his future endeavours.