During January 2016, the media linked Coventry's young midfield startlet James Maddison with £7million moves to Tottenham, Liverpool and Arsenal so it was a surprise when David McNally announced just as the transfer window closed at 11pm on Monday 1st February 2016 that Norwich had signed Maddison from Coventry on a three-and-a-half year contract for an undisclosed fee. This was reproted to be £2.5million. He was immediately loaned back to Coventry City for the remainder of the 2015/16 season. He scored once in 11 appearances on loan.
Maddison is a product of Coventry's youth team. After impressing for the club's under-18 side at the start of the 2013/14 season, Maddison was rewarded with a squad number and a place on the bench for the team's trip to Stevenage on 5th October 2013. He made his professional debut as a substitute on 13th August 2014 in a 2-1 League Cup loss to Cardiff City. He went on to make 31 appearances for the Sky Blues, scoring 4 goals, ahead of his move to Norwich.
Maddison made his Norwich debut on 23rd August 2016 in the 6-1 win over Coventry at Carrow Road in the Football League Cup. After impressing in the 6-1 win over Peterborough on 30th August 2016 in the Football League Trophy, scoring once, he was surprisingly loaned to Scottish side Aberdeen on 31st August 2016 until January 2017. "I am really excited to get James," said Aberdeen manager Derek McInnes. "James is a player with great talent and hopefully playing with us he will get a chance to showcase that. He can play in a number of positions in midfield and he is also a creative player. He is very good technically, he can make the difference in a tight game and is someone who I really hope will enjoy himself here. James is coming up to play with some very good players which he recognises. He recognises the demands of the club but all that was a big attraction for him. There were a lot of clubs interested in him because he is a good player but when we spoke to his agent and to James it was clear they seen Aberdeen as the preferred option which pleases me no end. He is here until January. We are comfortable with that and so are Norwich. We will see what transpires from there."
Maddison made 17 appearances for Aberdeen, scoring twice and playing in the final of the Scottish League Cup final (a 3-0 defeat to Celtic), before returning to Carrow Road. He made his first Championship appearance for Norwich as a substitute in the 3-1 win over Preston on 17th April 2017 with Maddison scoring Norwich's third goal. He finished the season with four appearances and one goal to his name.
Maddison's form in the first half of the 2017/18 season saw him linked with big money (£20m) moves to the likes of Liverpool, Tottenham, Crystal Palace, West Ham, Everton and Wolves. He finished the season as Norwich's player of th eyear, scoring 13 goals in 38 appearances. This speculation continued into the Summer 2018 transfer window with Everton, West Ham, Southampton, Fulham and Leicester being linked before he finally joined Leicester on 20th June 2018 for an undisclosed fee rumoured to be worth up to £24milion - Norwich's record sale. This is the largest ever Championship transfer deal for a player yet to feature in the top flight
Maddison made his debut for England's Under-21s as a 81st substitute in a 2-0 win in Ukraine in a European Championship qualifier,
Maddison's impressive start to the 2018/19 season for Leicester saw him called up to the England squad at the beginning of October 2018. He had played just eight Premier League games, scoring three goals.