Middlesbrough are monitoring Leicester City midfielder as a key figure nears a £25m move to Everton.

Middlesbrough are reportedly weighing up a move for Leicester City midfielder Oliver Skipp as preparations begin for the expected departure of Hayden Hackney, who appears increasingly close to completing a high-profile transfer to Everton.

Hackney has been one of Middlesbrough’s standout performers in recent seasons, and speculation surrounding his future has intensified ever since the club failed to secure promotion to the Premier League. Following defeat in the Championship play-off final, many expected the talented midfielder to attract strong interest from top-flight clubs, and that prediction now appears to be coming true.

Throughout the summer transfer window, Hackney has been linked with several Premier League sides eager to strengthen their midfield options. However, Everton have consistently emerged as the club showing the strongest interest, with reports suggesting the Merseyside outfit have made significant progress in negotiations.

Oliver Skipp (left) could potentially replace Hayden Hackney (right) at Middlesbrough. | Joe Giddens/PA Wire & Richard Sellers/PA Wire

According to The Telegraph, Hackney is now closing in on a transfer worth around £25 million. Everton are believed to have had multiple bids rejected by Middlesbrough during discussions, but the two clubs are reportedly edging closer to reaching a full agreement.

The report suggests that a breakthrough could arrive later this week, with all parties hopeful that the deal can be completed without unnecessary delays. Should the transfer go through, Middlesbrough would lose one of their most influential players, but they would also receive a substantial transfer fee that could be reinvested into strengthening the squad ahead of the new campaign.

With Hackney seemingly on the verge of leaving the Riverside Stadium, Middlesbrough have already begun identifying potential replacements capable of filling the sizeable void his departure would create.

Among the names under consideration is Leicester City midfielder Oliver Skipp.

The former Tottenham Hotspur academy graduate has reportedly attracted Middlesbrough’s attention as the club assesses its options in central midfield. Skipp is believed to be open to leaving Leicester this summer after enduring two hugely disappointing seasons with the Foxes.

Since arriving at the King Power Stadium, Skipp has experienced successive relegations, with Leicester dropping from the Premier League before suffering another demotion into League One. Those disappointing campaigns have significantly altered the midfielder’s situation, and he is now thought to be keen on finding a fresh start elsewhere.

Skipp joined Leicester from Tottenham in the summer of 2024 after completing a move worth approximately £20 million. At the time, the transfer was viewed as a smart acquisition for Leicester, with the midfielder arriving as a player who had already accumulated valuable Premier League experience despite still being in his mid-twenties.

Before leaving Spurs, Skipp had established himself as a dependable squad member under several managers. Having progressed through Tottenham’s youth system, he made more than 100 appearances for the North London club across all competitions, demonstrating his reliability, tactical discipline and ability to perform in different midfield roles.

His reputation had been enhanced even further by a highly successful loan spell at Norwich City during the 2020/21 campaign.

Playing under current Leeds United manager Daniel Farke, Skipp became one of the Championship’s standout midfielders as Norwich secured promotion to the Premier League by winning the league title. His energetic displays, intelligent positioning and composure on the ball earned widespread praise throughout that season, establishing him as one of England’s most promising young midfield players.

Oliver Skipp suffered relegation from the Championship with Leicester City last season. | Joe Giddens/PA Wire

Although his fortunes have dipped since moving to Leicester, many still believe Skipp possesses the quality required to thrive at Championship level, particularly within a side aiming to challenge for promotion.

That is one of the reasons Middlesbrough are reportedly monitoring his situation closely.

However, completing a move may not prove straightforward.

According to the report, Leicester are currently valuing Skipp at around £15 million, a figure that has discouraged Middlesbrough from making an immediate move.

While Boro are expected to receive a sizeable fee from Hackney’s proposed transfer to Everton, they are believed to be reluctant to spend such a large portion of that income on a single replacement.

As a result, Middlesbrough are thought to be waiting to see whether Leicester soften their stance or reduce their asking price later in the transfer window.

Should that happen, Skipp could quickly emerge as one of Middlesbrough’s leading targets.

Despite Leicester’s recent struggles, many observers believe Skipp’s individual quality has not disappeared. Instead, his reputation has inevitably suffered because he has been part of a squad that has endured consecutive relegations.

Players involved in unsuccessful teams often see their market value and public perception decline, regardless of their personal performances. Middlesbrough may therefore believe they have an opportunity to sign a player whose ability exceeds his current reputation.

If Skipp were to arrive at the Riverside Stadium, he would bring a wealth of experience for someone still only 25 years old.

Alongside his extensive Premier League appearances with Tottenham, he also understands what it takes to earn promotion from the Championship after playing such an important role during Norwich City’s title-winning campaign.

Those experiences could prove invaluable for a Middlesbrough side determined to mount another serious challenge for promotion after falling short last season.

Much will ultimately depend on whether Hackney’s expected move to Everton is finalised and whether Leicester become more flexible over Skipp’s valuation.

For now, Middlesbrough appear focused on planning for life without one of their brightest academy graduates while exploring the market for a midfielder capable of stepping into a crucial role. Oliver Skipp has emerged as a genuine option, but unless Leicester lower their reported £15 million asking price, any deal could remain difficult to complete.

With negotiations over Hackney’s future progressing and Middlesbrough actively assessing replacements, the coming days could prove pivotal in shaping both clubs’ transfer business ahead of the new Championship season.