Oliver Skipp’s departure from Tottenham Hotspur marks another significant step in Ange Postecoglou’s ongoing efforts to reshape his squad ahead of the new Premier League season.
The 23-year-old midfielder, who has been a part of Tottenham’s setup since joining the academy at the age of five, is set to make a permanent move to Leicester City, with reports suggesting that a deal in excess of £20 million has been agreed upon between the two clubs.
The transfer is a significant one for both Skipp and Tottenham. For Skipp, it offers a fresh start and the opportunity to establish himself as a key player at a club that is looking to rebuild after a challenging few seasons. Leicester City, relegated at the end of the 2023/24 season, are aiming for a swift return to the Premier League, and the addition of Skipp to their squad could be a crucial piece of the puzzle in achieving that goal.
For Tottenham, Skipp’s departure is part of a broader strategy by Postecoglou to revamp the squad and build a team capable of competing at the highest level. Skipp, despite being a highly regarded product of the club’s academy, struggled to secure regular playing time under Postecoglou last season. He made 24 appearances across all competitions but was primarily used as a substitute, with only seven of those appearances coming as starts in the Premier League.
The move to Leicester City represents a new chapter in Skipp’s career, one that could see him take on a more prominent role than he has been able to at Tottenham. Skipp’s time at Spurs has been one of mixed fortunes. Since making his first-team debut in 2018, he has shown glimpses of the talent that made him one of the most promising young players to come through the club’s academy in recent years. His loan spell at Norwich City during the 2020/21 season was a particular highlight, with Skipp playing a key role in the Canaries’ successful campaign that saw them promoted back to the Premier League.
However, despite the promise he showed at Norwich, Skipp found it challenging to translate that form into a regular starting role at Tottenham. The arrival of Postecoglou, who has his own ideas about how he wants his team to play, further limited Skipp’s opportunities. With Tottenham looking to rebuild and compete for a place in the top four, Skipp’s departure is seen as a necessary step in freeing up both space in the squad and funds for further reinforcements.
Leicester City, on the other hand, are getting a player who, at just 23 years of age, still has a lot of potential to develop. Skipp is known for his tenacity, work rate, and ability to break up play, qualities that will be highly valued in Leicester’s midfield. The move will also reunite Skipp with former Tottenham teammate Harry Winks, who made a similar move to Leicester last summer. Winks had a solid first season with the Foxes, and his presence could help Skipp settle in quickly at his new club.
This transfer also has emotional significance for both clubs. For Tottenham, letting go of a homegrown player like Skipp is never easy, especially one who has been with the club for so long. However, with the club’s ambitions in mind, it is a decision that makes sense. Skipp himself has reportedly said his goodbyes to his Tottenham teammates, indicating that he understands the necessity of this move for his career.
Leicester City, meanwhile, are in the midst of a major rebuilding process following their relegation. The addition of Skipp, alongside Winks, is a clear indication of the club’s intent to build a strong squad capable of competing in the Championship and securing an immediate return to the Premier League. The reported £20 million fee also represents a significant investment by Leicester, signaling their confidence in Skipp’s ability to be a key player for them.
Oliver Skipp
As Tottenham prepare to face Leicester in their Premier League opener on Monday, the match will have added significance for both clubs. While Skipp will not be eligible to play, having missed the registration deadline, the fixture will be a chance for both teams to showcase their new-look squads. For Tottenham, it will be an opportunity to see how Postecoglou’s reshaped side performs in a competitive setting. For Leicester, it will be the beginning of their journey to bounce back from the disappointment of relegation.
James Maddison, who made the switch from Leicester to Tottenham in a £40 million move last summer, is also set to face his former club for the first time. Maddison had a strong start to his Tottenham career, but injuries hampered his progress towards the end of the season. His return to the King Power Stadium will be closely watched, as Leicester fans will be keen to see how their former star performs against them.
In the build-up to the match, Postecoglou emphasized the importance of improvement and consistency in his team’s performances. “I go into every season with the same kind of target of trying to be successful. The starting point for us is improvement. Improvement in our football, improvement in the consistency of our football,” he said. Postecoglou’s focus on continuous improvement suggests that he is looking to build a Tottenham team that can not only compete at the top level but do so consistently over the course of a season.
The departure of Oliver Skipp, while bittersweet for Tottenham fans, is a necessary part of this process. It allows both the player and the club to move forward in their respective journeys. For Skipp, the move to Leicester City offers the chance to reignite his career and fulfill the potential he has shown in flashes during his time at Tottenham. For Tottenham, it is another step towards building a squad capable of achieving the club’s ambitious goals under Postecoglou’s guidance. As the new season kicks off, both Skipp and Tottenham will be looking to make the most of the opportunities that lie ahead.
