Tottenham are attempting to beat competition from Liverpool, Everton, Manchester City and Newcastle for the Coventry prospect.
The Times describe Maddison as 'the new Dele Alli', and claim David Pleat, part of Tottenham's transfer committee, has scouted the youngster extensively.
Manchester City, Newcastle, Everton, Liverpool and Southampton are all credited with interest, but Spurs are said to be aiming to steal a march on their competitors by submitted a bid this month.
So who is James Maddison?
Maddison is 19-years-old and plays in an attacking midfield role, and would compete with Christian Eriksen, Alex Pritchard and Josh Onomah for position at Spurs.
He has graduated through the Sky Blues youth system and is currently playing alongside Joe Cole.
Currently his contract takes him up until June 2018, meaning Coventry are under no immediate pressure to cash in, but financially there is only so much resistance they could withstand.
Coventry are in the midst of a promotion battle, presently in fourth place in League One, and for this reason Spurs could attempt to sweeten a deal as they did with Alli last season by permitting him to remain at the club until the end of the season on loan.
This season he has made 10 first team appearances, scoring two goals and providing three assists.