Oliver Skipp was one of Tottenham Hotspur’s most promising academy talents, but he moved to Leicester City after failing to nail down a regular starting place.

Oliver Skipp is a midfielder who currently plays for Leicester City in the Premier League.

The midfielder joined Spurs in August 2018 from grass-roots club Bengeo Tigers FC and had an encouraging first impact.

He went on to make his debut for the club two months after joining, and since signing in North London, Skipp represented England under-21s for the first time.

The midfielder played a key role in Norwich City's return to the Premier League in 2020/21, after joining the club on loan.

Skipp started to make regular appearances for Tottenham over the following two seasons, but he became a bit-part player under Spurs boss Ange Postecoglou during the 2023/24 campaign and joined Leicester City in August 2024 in a deal worth £25million.

 

Tottenham Hotspur debut

After signing for Spurs in August 2018, it would only take Skipp until October to claim his first first-team appearance.

The midfielder came on for the last six minutes in his sides 3-1 EFL Cup victory over West Ham United. In that competition he would only play once more - appearing for a minute against Chelsea in the semi-final first leg.

When Skipp wasn't participating with the first team he would be playing in the UEFA Youth League and Premier League 2. However, his academy responsibilities were to be dropped as he would become a regular within Spurs' travelling squad.

The Englishman sat on the bench for Premier League games against Cardiff and Wolves, but on the 8th of December, Skipp made his top flight debut, replacing Kieran Trippier in the 87th minute against Southampton.

He would make his first Premier League start two games later in a 1-0 win over Burnley and would continue to appear against the likes of Everton, Bournemouth, Cardiff, and Leicester.

Skipp claimed his first senior goal contributions in Spurs' FA Cup fixture against Tranmere Rovers, as he assisted two of the seven goals put past the opposition.

In his debut season, Skipp made a total of 12 appearances for the first team aged 18 and would continue this into the 2019/20 campaign.

Skipp made one fewer appearance in the following season, however he made his Champions League debut in a 4-0 win over Red Star Belgrade November 2019.

After being promoted fully to the senior side he would later leave Spurs on a loan move that would aid the youngsters development.

Promotion with Norwich City

Skipp signed on loan for Norwich City before the start of the 2020/21 Championship campaign with the crucial aim of reclaiming their place in the top flight.

Skipp started off his season with a bang as the Englishman was awarded Norwich City's Falcon Power Player of the Month for September as his side won, drew, and lost once during their opening three games.

In this season, Skipp went onto score his first and currently only senior goal within soccer. His 90+5 minute goal against Birmingham secured a 3-1 win as the Canaries pushed for automatic promotion.

The Englishman also bagged two assists late on in the season, one in a 2-1 win over Sheffield Wednesday, another in a 7-0 battering of Huddersfield.

And after winning 29, drawing 10, and losing seven, Norwich City and Skipp were crowned champions of the Championship, finishing six points above Watford.

His efforts and performances in the Championship even earned him a spot in the PFA's Team of the Year for the 2020/21 season.

Skipp played a total of 3,892 minutes while on loan in Norfolk, the most in one season for the Spurs man.

 

Moving to Leicester City

After proving himself on loan at Norwich, Skipp became more involved in the first team setup at Tottenham, playing more frequently under managers Nuno Espirito Santo and Antonio Conte.

However, after the arrival of Ange Postecoglou he only had a bit-part role in the 2023/24 season.

On August 19, 2024, Leicester completed the signing of Skipp on a five-year contract.

The deal for the 23-year-old was understood to be an initial £20million with a further £5m in add-ons.

Skipp’s departure from Tottenham ends an association which began when he joined their academy aged six, going on to make 106 first-team appearances.

“I’m really excited to sign. I’ve got the feeling that it’s a good group of people and a good group of players,” Skipp told the club’s website.

“I had conversations with the people here and they gave me a feeling of warmth and that they were excited to have me on board.

“As a player, when you feel that excitement, that’s something you can use to develop your game.

“The staff here know me as well – Steve (Cooper), I have worked with at England so there’s definitely a good relationship there and I’m keen to push on and show what I can do.”

 

International career

From then on, Skipp has played another 13 times for the national side, even participating in the 2021 UEFA European Championships, in which Skipp played every minute of their three group stage matches, before being knocked out.

Personal life

From 2003 to 2012, he attended Duncombe Primary School and Richard Hale School.

 

Net worth

Oliver Skipp's net worth is reported to be £800,000.