Coventry City Maddison joined
Coventry City's youth team, and was included in the first-team squad in the
2013–14 season, though did not make an appearance. He made his first-team debut in August 2014, coming on as a
substitute in a 2–1 defeat to
Cardiff City in the
2014–15 League Cup. Maddison made his league debut, again as a substitute, in a 3–1 home loss against
Bristol City and his first league start in the following game, against
Oldham Athletic. He scored his first league goal in the game, with a
free kick in the first half, as Coventry lost the game 4–1. In November 2014, Maddison signed his first professional contract, lasting three and a half years, but missed much of the remainder of the
2014–15 season after being sent off during a Boxing Day defeat to
Doncaster Rovers and then picking up a back injury.
Norwich City Maddison signed for
Premier League club
Norwich City on 1 February 2016 on a three-and-a-half-year contract for an undisclosed fee, but was immediately
loaned back to Coventry City for the remainder of the
2015–16 season. Maddison made his debut for Norwich on 23 August 2016 in a
2016–17 EFL Cup tie against his former team Coventry, recording two assists in a 6–1 home win. On 31 August 2016, Maddison was loaned to
Scottish Premiership club
Aberdeen for the first part of the
2016–17 season. He made his debut as a substitute against
Inverness Caledonian Thistle, then started and scored in the next match in a 3–1 win against
Dundee. He followed this with a last-minute winner against
Rangers on 25 September. He made 17 appearances for Aberdeen, scoring two goals. He signed a new four-year contract with Norwich in June. With the arrival of new coach
Daniel Farke, Maddison was given regular starts in the team during the
2017–18 season. He was named as Norwich's
Player of the Season at the end of the season, and was nominated for the EFL Championship Young Player of the Season award.
Leicester City in 2021 Maddison signed for Premier League club
Leicester City on 20 June 2018 on a five-year contract for an undisclosed fee thought to be around £20 million. He scored his first goal in the Premier League on 18 August in a 2–0 win against
Wolverhampton Wanderers. He later followed up his impressive start for the club with back-to-back Premier League goals, both from set-pieces, against
AFC Bournemouth and
Huddersfield Town, respectively. His performances in his
debut season saw him awarded Leicester City's Young Player of the Season. On 29 July 2020, he agreed a new four-year contract with Leicester. On 27 September 2020, Maddison scored from long range in a 5–2 win against
Manchester City, a goal which was later voted as
Premier League Goal of the Month. On 11 April 2021, Maddison was one of three players dropped from Leicester's squad for the game against
West Ham United after breaching
COVID-19 protocols. On 15 May, he appeared as a substitute in the 67th minute of the
2021 FA Cup Final, as Leicester beat
Chelsea 1–0 at
Wembley Stadium. He top scored for the team with 18 goals in all competitions, in addition to registering 12 assists. On 11 February 2023, Maddison
captained Leicester for the first time in a 4–1 win over
Tottenham Hotspur, a match in which he scored his team's second goal and assisted their fourth. He ended the
2022–23 season with ten goals and nine assists in the
Premier League as Leicester were relegated to the
Championship.
Tottenham Hotspur 2023–24 On 28 June 2023, Maddison signed for Premier League club
Tottenham Hotspur on a five-year contract for an undisclosed fee. The transfer fee was reported to be £40 million. On 12 August, Maddison was appointed as
vice-captain alongside
Cristian Romero, with
Son Heung-min as
club captain. Maddison made his debut for Tottenham on 13 August in the team's opening match of the
2023–24 Premier League season, starting in an away match against
Brentford. He scored his first goal for the club on 26 August in a 2–0 away win against Bournemouth. Registering one goal and two assists in his first three league matches for Tottenham, Maddison was named the
Premier League's Player of the Month for August. On 6 November 2023, Maddison was forced off with an ankle injury in a home match against Chelsea, which was expected to keep him on the sidelines until 2024. He returned from injury as a substitute in a 1–0 loss to Manchester City in the FA Cup on 26 January 2024. Maddison would struggle for form through the rest of the season, scoring only 1 more goal in Tottenham's 0-4 away win against
Aston Villa, as well as providing 4 assists in Tottenham's 17 remaining Premier League matches.
2024–25 . Maddison would score his first Premier League goal of the
2024-25 season on 29 September in a 3-1 home win over Brentford, maintaining a period of good form through the first 4 months of the season, including scoring 2 goals in Tottenham's 0-4 away win against
Manchester City on his 28th birthday. He would score his first
Europa League goal for Tottenham in their 2-3 league phase away win against
Hoffenheim on 23 January 2025, also providing an assist for Son Heung-min. Maddison suffered a calf strain in January 2025 following the Europa League match against Hoffenheim, being out for 3 weeks before returning on 16 February for Tottenham's 1-0 home league win against
Manchester United, where he scored the only goal of the match. In April, Maddison would assist
Pedro Porro's goal against
Eintracht Frankfurt in the first leg of the Europa League quarter-final, as well as win the penalty for
Dominic Solanke in the second leg. On 1 May, during the Europa League semi-final first leg against
Bodø/Glimt Maddison would score in the 34th minute, though would be substituted for
Dejan Kulusevski in the 65th minute. It was confirmed by Tottenham head coach
Ange Postecoglou on 4 May that Maddison had suffered a knee injury that would bring an end to his season.
2025–26 Maddison returned for
2025–26 pre-season, but sustained another knee injury during a friendly against
Newcastle United. New Spurs head coach,
Thomas Frank, described the injury as "bad" and a "brutal moment". It was later revealed that he had suffered an
ACL injury, which would sideline him for most of the upcoming season. ==International career==