Maddison, 26, flew to London from Ibiza on Tuesday and has already agreed personal terms on a long-term contract with Spurs in a major coup for new head coach Ange Postecoglou.
Winks, who came through Spurs’ academy and has made 128 appearances for the club in all competitions, is closing in on a permanent move to the Foxes, having spent last season on loan at Italian club Sampdoria.
Maddison will add spark and creativity to a Spurs attack already boasting Harry Kane, Heung-min Son, Richarlison and Dejan Kulusevski, although the England captain’s future remains in doubt following a £60m bid from Bayern Munich
Spurs insist they do not want to sell Kane, who is said to be open to joining the perennial Bundesliga champions, but they would have to consider a mammoth offer in the region of £100m or more for the 29-year-old, who has entered the final year of his contract.
Newcastle were also pursuing Maddison, who had a year remaining on his Leicester deal, but cooled their interest after signing AC Milan’s Sandro Tonali, leaving Spurs able to negotiate down the Foxes’ £50m asking price following talks this week.
Spurs have tracked Maddison since he was at Coventry but missed the chance to sign him in 2016, when he joined Norwich, and again two years later when he moved to the King Power Stadium in deal worth around £20m.
At Leicester, he has established himself as one of the top creative players in the Premier League, last season finishing with 10 goals and nine assists in the top flight despite the Foxes’ relegation.
His form earned him a surprise call-up to Gareth Southgate’s squad for the World Cup but he did not feature in Qatar due to injury and earned his third England cap in this month’s qualifying win in Malta.
He has made 203 appearances in all competitions for Leicester, helping them to the 2021 FA Cup, and scoring 43 League goals – around one every 3.7 games.
Postecoglou has favoured a 4-3-3 formation and Maddison is most likely to line up as one of his No8s in midfield but could also operate on either side of the front three.
Maddison is Spurs’ second new signing of the summer after the £17.2m capture of goalkeeper Guglielmo Vicario on a five-year deal, while Kulusevski’s loan move from Juventus has been made permanent.
They are in the market for a centre-back, with talks continuing for Bayer Leverkusen’s Edmond Tapsoba and interest in re-signing Clement Lenglet, who spent last season on loan from Barcelona.
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