Career
Coventry City
= 2013-2014 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. = 2014-2015 Maddison made his professional debut as a substitute on 13 August 2014 in a 2-1 League Cup loss to Cardiff City, coming on to replace Josh McQuoid after 69 minutes. After coming off from the bench to assist Shaun Miller for Coventry City"s only goal in a 3-1 defeat to Bristol City at the Ricoh Arena, Maddison was handed his first league start for the following league game away to Oldham Athletic.
Maddison went on to score his first league goal for Coventry City with a free-kick in the first-half, his efforts were in vain as the Sky Blues went on to lose the game 4-1.
On 24 November 2014 the club announced they had offered the player his first professional contract, lasting three and a half years. Maddison missed a large portion of the 2014/15 season after being sent-off during a Boxing Day defeat to Doncaster Rovers before picking up a back injury.
Maddison returned to the first-team as a substitute during a 0-0 draw with N ottinghamshire County in April 2015. Maddison grew into an increasingly important role in the team towards the end of the 2014-2015 season which was capped off with a winning goal on the final-day against Crawley Town.
= 2015-2016 After continuing to impress Coventry City manager Tony Mowbray over the following pre-season, James Maddison was handed the number 10 jersey for the 2015/16 season.
Norwich City
On 1 February 2016, Maddison joined Norwich City on a three-and-a-half year contract for an undisclosed fee he was immediately loaned back to Coventry City for the remainder of the season.