Since the Coventry-born midfielder posed for photographs at the Club's former first-team base at Belvoir Drive on that day in 2018, Maddison has cemented his status as one of English football's most accomplished stars. He's won the FA Cup and the FA Community Shield and also represented England.
The signs were there when City opened the 2018/19 Premier League season away at José Mourinho's Manchester United. The Club's new No.10 sparkled for just over an hour, although the Foxes fell to a spirited 2-1 defeat at Old Trafford under the management of Claude Puel.
James Maddison joined the Foxes after an impressive year in the second tier with Norwich City.
His home debut included a landmark moment, as Maddison bended a well-struck, right-footed drive into the bottom corner in a 2-0 victory over Wolverhampton Wanderers. Goals against AFC Bournemouth and Huddersfield Town soon followed as the former Aberdeen loanee settled in.
In December, one of the finest goals of recent seasons came as Maddison chested down a Marc Albrighton cross, took it under control with his thigh and belted a half-volley beyond Ben Foster in a 2-0 win against Watford at King Power Stadium. He would end his debut top-flight campaign with eight goals.
With Brendan Rodgers now in charge, the 2019/20 season allowed Maddison to acclimatise further in the big league. As City embarked on a Club-record eight-game winning run, including that historic 9-0 triumph over Southampton at St. Mary's Stadium, Maddison was shining bright in Leicester blue.
A brilliant half-volley against Watford offered an early glimpse of Maddison's quality.
His stunning free-kick on that wonderful night on the south coast applied a splash of stardust to proceedings. He added another memorable effort, a rocket-like strike on Filbert Way, in a 2-0 win over Arsenal two weeks later. Leicester would end the year in fifth place, returning them to the European stage.
It was also a year which included the fulfilment of a childhood dream for City's No.10 – as he replaced Alex Oxlade-Chamberlain to make his senior debut for England as Gareth Southgate's Three Lions ran out as 7-0 winners over Montenegro at Wembley Stadium.
Matches were being staged behind closed doors, due to COVID-19 safety measures, by the time the 2020/21 season begun in September. The month would end in extraordinary fashion for the Foxes, with Maddison picking out the top corner in a magnificent 5-2 away comeback win at Manchester City.
Maddison then found the net in 3-0 and 4-0 successes over Zorya Luhansk and Braga respectively in the UEFA Europa League group stage, before delivering a memorably superb display in a 3-0 win against Brighton & Hove Albion in December – striking twice for Rodgers' men at King Power Stadium.
Maddison superbly curled into the top corner at Etihad Stadium during Leicester's 5-2 win over Manchester City.
In the New Year, he scored in four successive games. They came as City scooped the maximum nine points from Newcastle United, Southampton and Chelsea, while also seeing their way past Brentford in the FA Cup. A 3-1 win over Liverpool in February again featured Maddison's name on the scoresheet.
Rodgers has been keen for Maddison to provide a presence at both ends of the pitch and that development was on show during the Club's appearance in the final of the FA Cup in May 2021. Youri Tielemans stole the headlines, but the application of Maddison and Co. shouldn't go unnoticed.
Lifting major silverware in Leicester City colours.
The confident 25-year-old was an FA Cup winner and would soon add the FA Community Shield to his individual honours list as champions Manchester City were also beaten at Wembley three months later. It was the first act of what would become a profitable campaign for the attacking midfielder.
Although waiting until October for his first goal, the winner in a 2-1 success at Brentford, the 2021/22 season would end with Maddison's best-ever goalscoring total. In fact, as well as hitting the target 18 times, he became the first LCFC player since Riyad Mahrez to register double figures in goals and assists.
A goal and a win in the quarter-finals of the UEFA Europa Conference League for Maddison at PSV Eindhoven.
Whether it was stunners at Anfield or in Randers, crucial strikes in Eindhoven or at Stamford Bridge, Maddison's quality was on show to all. City would reach the semi-finals of the UEFA Europa Conference League too – the deepest the Club has ever advanced in a European competition.
In May, on the other hand, personal recognition would arrive in the form of winning the Club's Mens Player of the Season prize, voted for by the Blue Army. It's clear that City's No.10 is only getting started.
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