The England international, who only has one year left on his contract, has been attracting plenty of interest but Spurs were effectively given a free run at him after Newcastle prioritised a move for AC Milan’s Sandro Tonali instead.
Leicester were initially demanding a fee in the region of £60m for Maddison despite their relegation and the player’s precarious contract situation, but have now softened that stance.
The 26-year-old had been on holiday in Ibiza but flew to London on Tuesday and will undergo a medical on Wednesday after the two clubs agreed a £40m deal.
In a separate transfer, Winks – who spent last season on loan in Serie A with relegated Sampdoria – will move to the King Power Stadium in a deal that could reach £10m.
That means Tottenham have effectively landed Maddison for £30m plus Winks in a deal that could well represent one of the bargains of the summer.
New manager Ange Postecoglou is a big fan of the attacking midfielder and quickly identified him as a key signing as he looks to bring more creativity into the Tottenham team.
Although Leicester were relegated last season, Maddison was a lone bright spark and finished the campaign with 10 goals and nine assists.
He managed 20 combined goals and assists in the 2021-22 campaign and his consistency over the past two years saw him finally earn a call-up to Gareth Southgate’s England squad.
After a three-year absence, Maddison was part of the squad that went to Qatar at the end of last year – though did not make an appearance at the World Cup – while he impressed in Euro 2024 qualifiers against Ukraine and Malta.
Maddison is set to become Spurs’ third signing of a busy summer, with the club already securing a £17m deal for goalkeeper Guglielmo Vicario as well as turning Dejan Kulusevski’s loan move into a permanent stay.
Their spending is unlikely to stop there, either, with Postecoglou now looking to focus on bolstering a back-line that conceded 63 goals in the Premier League last season.
Talks are believed to be taking place to secure a deal for Bayer Leverkusen’s imposing centre-back Edmond Tapsoba, while Wolfsburg’s pacey Dutch defender Micky van de Ven is also on the north Londoners’ radar.
MORE : Tottenham confirm £17m arrival of Guglielmo Vicario as details of Ange Postecoglou conversation emerge
MORE : Tottenham respond to Bayern Munich’s £60m Harry Kane bid as Thomas Tuchel makes his pitch
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