Oliver Skipp might depart before Leicester travels to Spain for the remainder of its pre-season, and Middlesbrough has been mentioned as a possible destination.

Middlesbrough have been linked this week with a move for Leicester City midfielder Oliver Skipp. The player is well known to Kieran Scott and head of recruitment Chris Jones, as both were involved in arranging his successful loan move to Norwich City in 2020-21.

Middlesbrough are reportedly interested in signing Oliver Skipp as a replacement for Hayden Hackney. John Percy reports that Skipp could leave Leicester for Middlesbrough, but the club is deterred by the £15 million asking price. Percy states that Skipp wants to leave Leicester and restart his career after the club's relegation to the third tier, and that the potential transfer fee is causing Middlesbrough to consider other targets. Leicester are under pressure to sell players to fund their own signings under new manager Russell Martin, and Skipp is one of the players they are seeking to sell. Skipp's wages are also considered a potential obstacle. According to estimates from Capology, Skipp earns a wage of £50,000 per week. Luke Ayling is the highest-paid permanently contracted player at Middlesbrough, earning £30,000 per week. It is suggested that an agreement could be reached for a loan deal for Skipp, but not for a permanent transfer for £15 million.

According to John Percy of The Telegraph, Middlesbrough are in talks with Leicester City for Oliver Skipp, who is a 25-year-old English midfielder. It is reported that Middlesbrough are deterred by the initial £15 million valuation from Leicester. Leicester were recently relegated to League One. Skipp joined the club for over £20 million in the summer of 2024, and his contract with Leicester runs until 2029. Following their relegation, it is anticipated that many players will leave the club, and Skipp is expected to be one of them. In the 2025/2026 Championship season, Skipp made 34 appearances and scored one goal. He has 24 caps for the England U21 team, and his current Transfermarkt market value is €4.00m.