Tottenham Hotspur Skipp started his youth career with Bengeo Tigers FC in Hertford before joining
Tottenham Hotspur in 2008. On 29 August 2018, Skipp signed a three-year contract with Tottenham. He made his professional debut for Tottenham in a 3–1
EFL Cup win over
West Ham United on 31 October. He made his league debut in a home match against
Southampton, coming on as a late substitute in a 3–1 win, and made his first start on 15 December in a 1–0 win against
Burnley. In January 2019, Skipp assisted two goals in Tottenham's 7–0 win against
Tranmere Rovers in the
FA Cup. On 17 July 2020, Skipp signed a new three-year contract with the option of a fourth with Tottenham. For the 2020–21, season he joined
Norwich City on loan. Skipp scored the first goal of his career in Norwich's 3–1 win at
Birmingham City on 23 February 2021. Skipp went on to help Norwich win the Championship and was included in the 2021 PFA Team of the Year. Skipp established himself as a regular starter for Tottenham in the first half of the 2021-22 season, making 18 appearances before suffering a pelvic injury in January, which saw him miss the rest of the season. On 20 April 2022, Skipp signed a new five-year contract with Tottenham that is set to expire in 2027. Skipp made his return from injury in a pre-season friendly on 13 July 2022.
Leicester City On 19 August 2024,
Leicester City announced that they had reached an agreement with Tottenham Hotspur to sign Skipp on a five-year deal for a £20 million
transfer fee. He made his debut for the club on 24 August 2024 in a 2-1 defeat to
Fulham, coming off the bench in the 71st minute. ==International career==