On 17th August 2020 Norwich secured the loan signing of Tottenham midfielder Oliver Skipp for the 2020/21 season, against the wishes of manager Jose Mourinho who admitted he was selfish in wanting to keep Skipp around the first team squad as he saw him as a future Spurs captain but grudginly recognised and agreed with Skipp that a loan to gain playing time was needed at this stage of his career.

Born in Welwyn Garden City and raised in Hertfordshire, Skipp played for the Bengeo Tigers youth team before joining Spurs in 2013. He progressed through the youth team ranks before signing a professional contract in August 2018. He made his professional debut for Spurs on 31st October 2018 in the League Cup against West Ham and then made his league debut against Southampton. By the time he joined Norwich, he had made 23 appearances for Spurs. He scored his first goal for Spurs in the 7-0 win over Tranmere in the FA Cup in January 2019.

He has been capped by England at Under-16, Under-17 and Under-18 level before winning his first Under-21 cap against Slovenia in October 2019. Whilst on international duty, he was with Norwich players Todd Cantwell, Max Aarons and Ben Godfrey who influenced his decision to join Norwich.

Skipp made an impressive debut for Norwich, winning the Man of the Match award, on 12th September 2020 in the 1-0 away win at Huddersfield on the opening day of the 2020/21 league campaign. He scored his first senior goal on 23rd February 2021 in the 3-1 away win at Birmingham. Skipp charged forward on the counter-attack alongside Lukas Rupp, and the latter selflessly played the ball across to him to tap into an empty net in the fifth minute of stoppage time. He said “When there’s a goal at stake, and I don’t get many, I saw Lukas and the ball was bouncing so I thought ‘he’s got a good chance of winning this. It was brilliant from Lukas to have the awareness one-on-one just to lay the ball off. It shows the selflessness of him and made it simple for me so I can only thank him for that. It’s nice because I don’t get many so that’s one that I’ll cherish! I haven’t scored in senior football! It’s definitely one that I’ll remember, but more importantly three points and another step closer to what we want to achieve, so it’s not just about me.”

His impressive form for Norwich saw him voted third in the Barry Butler trophy for Norwich's Player of the Season at the end of April 2021. Skipp made 47 appearances for Norwich in 2020/21 as the Canaries won the Championship title. The Canaries then approached Spurs about loaning Skipp again for the 2021/22 Premier League campaign

In October 2021 he was named in World Soccer's Top 500 most important players in the world.

On 8th July 2023 Skipp came on as substitute in the 73rd minute for Angel Gomes as England's Under-21s won the European Under-21 Championships for the first time since 1984. They beat Spain 1-0 in the final held in Georgia. He played in six games, starting in one and coming on as substitute in five.

On 18th August 2024 he transferred to Leicester City for a fee in excess of £20million. He signed a five year contract. He had played 106 games for Spurs scoring once. He made his Leicester debut on 24th August against Fulham.