A summer acquisition from Norwich City in 2018, Maddison arrived in the East Midlands with a big reputation in the Sky Bet Football League and it didn't take long for the Coventry-born midfielder to make a name for himself at a higher level with the Foxes.
Since that switch to King Power Stadium, the 24-year-old has developed into one of the Premier League's most exciting attacking players and made his debut for the England senior team. On the three-year anniversary of his move, here are some of our favourite Maddison moments so far...
A stunner stings the Hornets
By the time Watford visited Leicester in December 2018, an array of sparkling performances had already endeared the Club's new No.10 to the Blue Army and pundits from afar were sitting up and taking notice too. The pick of his goals in that debut top-flight campaign was very special.
It came about when Maddison fed Jamie Vardy in the centre circle. A quick shimmy from Vardy allowed him to commute the ball wide to Marc Albrighton, who curled in a cross-field pass back to Maddison. A neat few touches, one off his chest, gave him time, before smashing it past Ben Foster on the volley.
Free-kick magic in Huddersfield
Goals from Youri Tielemans and Jamie Vardy had put Leicester two goals up at John Smith's Stadium, but an Aaron Mooy penalty made it a potentially nervous affair for the visitors in the second half. They needn't have worried, though, when Maddison stepped up to take a 79th-minute free-kick.
Just as he had done at Burnley earlier in the season, the former Aberdeen loanee picked his spot past former Leicester goalkeeper Ben Hamer with a sublime curler to make it 3-1 to Brendan Rodgers' men in Yorkshire. A late Vardy spot-kick made sure with six minutes to play.
Completing the comeback against Spurs
One of the defining moments of the 2019/20 season came on 21 September as Tottenham Hotspur visited King Power Stadium. Anxiety was in the air when former City loanee Harry Kane put Mauricio Pochettino's north London outfit ahead, only for Ricardo Pereira to level it up on 69 minutes.
Spurs, though, continued to threaten on Filbert Way. So, too, did Leicester, however. And in the 85th minute, Hamza Choudhury rolled the ball across the edge of the penalty area... teeing it up perfect for Maddison to come charging in, arrowing a sweetly-struck rocket into Hugo Lloris' bottom corner.
A record-breaking night in Southampton
Any evening which sees your club equal an all-time record for the biggest-ever Premier League victory and includes a brace of hat-tricks for two of your team-mates may relegate a solitary goal into insignificance. Not in the case of Maddison, though, in this breathtaking 9-0 triumph over Southampton in 2019.
Jamie Vardy and Ayoze Pérez netted three goals apiece for the Foxes, while Ben Chilwell and Youri Tielemans also got on the scoresheet, but the pick of the goals at St. Mary's Stadium came from a familiar source. With another exquisite free-kick, City's No.10 gave Angus Gunn no chance.
Sheer class at Etihad Stadium
Throughout the most recent 2020/21 campaign, many games have been defined by an individual moment of brilliance. In Leicester's 5-2 victory over future champions Manchester City at Etihad Stadium in the late summer of 2020, there were several, but Maddison wasn't going to miss out.
A second-half substitute in Manchester, as he recovered from injury, the 24-year-old emerged to add City's fourth of a delirious afternoon, whipping a sumptuous effort beyond Ederson and into the top corner. Sheer class from the England international.