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Tottenham have reportedly agreed to sell their 21yo defender to Middlesbrough in a deal worth up to £20 million, while retaining a 20% sell-on clause and matching rights. Tottenham Hotspur have completed the permanent sale of young defender Ashley Phillips to Championship side Middlesbrough in a deal that could eventually reach £20 million, according to updates shared by Hotspur Lane on X. The agreement is reportedly structured with £7 million guaranteed, while a further £13 million could be triggered through performance-related add-ons. Tottenham have also secured a 20% sell-on clause and matching rights, ensuring the club retains significant control over Phillips’ future should he continue his development. The deal represents a notable piece of business for Spurs, who signed the defender from Blackburn Rovers in 2023 before sending him out on loan to accelerate his progress. Tottenham secure long-term value from Ashley Phillips transfer While Phillips was regarded as one of England’s brightest defensive prospects, breaking into Tottenham’s first team has become increasingly difficult following the club’s extensive summer rebuild under Roberto De Zerbi. Spurs have strengthened their defensive options, including the arrival of Jan Paul van Hecke, while established names such as Micky van de Ven and Cristian Romero remain central to De Zerbi’s plans. As a result, Phillips faced limited opportunities for regular Premier League football. Rather than allowing the 21-year-old’s value to stagnate, Tottenham have opted for a deal that provides immediate financial return while preserving future upside through substantial add-ons and a 20% sell-on clause. The inclusion of matching rights also gives Spurs an advantage should another club attempt to sign Phillips later in his career. For Middlesbrough, the signing represents a major investment in one of English football’s highly rated young defenders as they look to strengthen their push for promotion to the Premier League. Meanwhile, Tottenham continue to balance squad improvement with financial sustainability. The structure of the Phillips transfer reflects the club’s growing emphasis on generating value from player trading while maintaining flexibility for future transfer windows.