Maddison, 28, picked up a knee injury in Tottenham’s 1-1 pre-season friendly draw with Premier League rivals Newcastle on Sunday (August 3).
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New manager Thomas Frank described it as ‘brutal’ and it remains to be seen how long the attacking midfielder will be out of action.
According to Sports Mole, Spurs wasted no time in entering the market for a replacement, reaching out to Man City for unwanted star Grealish.
The 29-year-old has struggled since making the move form Aston Villa for a reported fee of £100 million back in 2021, scoring just 17 goals in his 157 games across all competitions.