For Harry Kane, facing Arsenal has always felt personal. The dead-eyed determination that has transformed him into one of the world’s elite strikers for England, Tottenham Hotspur and now Bayern Munich can be traced back in no small part to the painful rejection he experienced from the Gunners as a young boy.

Kane joined Arsenal’s under-9s age group from Ridgeway Rovers — a grassroots club based in Chingford, Essex whose most famous alumnus other than Kane is David Beckham — but lasted a couple of years before receiving the first damning judgment of his career. Arsenal’s then academy boss Liam Brady later described Kane as “a bit chubby” and “not very athletic.”

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Roy Massey, assistant coach of the club’s academy from 1998 until 2014 claimed Kane offered to transform himself from a striker into a goalkeeper, so desperate he was to make the grade.

“I thought the least I could do was to send him to work with our keeper coach Alex Welch,” Massey said. “Alex was one of the best in the business and after just a few sessions he told me ‘Roy, the lad is never going to make the grade in goal’, so this time Harry had to move on. I know how much it hurt him.”

Kane returned to Ridgeway and resumed his career as a striker, scoring goals almost at will again to earn a six-week trial by Tottenham.

Spurs initially opted not to extend their interest but while on a subsequent trial at Watford, Kane scored a hat trick against them and Tottenham offered him a contract almost immediately. He was 11, starting a love affair with Arsenal’s closest rivals which would later blossom, via a circuitous route involving uneventful loan spells at Leyton Orient, Millwall, Norwich City and Leicester City.

Kane eventually broke into the first team in 2014 and would go on to become Tottenham’s all-time record goal-scorer before leaving for Bayern last summer in a deal worth up to €120 million.

King Kane at the Lane 👑#OnThisDay in 2015 @SpursOfficial surged back for a big north London derby win 👊 pic.twitter.com/QamM0Jqhh6

— Premier League (@premierleague) February 7, 2019

Tuesday’s Champions League quarterfinal first leg at Emirates Stadium sees Kane return to north London for the first time since his departure, still fuelled by that past disappointment and motivated by the ongoing quest to finally end his wait for a first major trophy.

Kane has not hidden his desire for revenge on Arsenal. In a 2018 letter written in The Players’ Tribune to mark his 100th Premier League goal, Kane recalled his first derby game against Arsenal in February 2015: a 2-1 win in which he scored both Tottenham goals.

“We were in the tunnel, and I thought: ‘OK. Took me 12 years. But we’ll see who was right and who was wrong,'” he wrote. “The winner in the 86th minute was something that I’d never even dream of visualizing before a match. It was a header — probably the best header I’ve ever scored — and that feeling when it hit the back of the net … I’ve never felt a rush like that in my whole career. I remember walking round the pitch after the final whistle … and clapping to the fans … and it felt like: ‘Well, I told you so.'”

It is a message he has sent with impressive regularity ever since. Nobody has scored more goals in north London derbies than Kane, netting 14 times in 19 games, seven of which were penalties.

As if to undermine the popular Tottenham chant of “Harry Kane, he’s one of our own” which provided the soundtrack to his emergence, pictures of the striker wearing an Arsenal shirt at the Gunners’ 2004 “Invincibles” league title parade emerged shortly after that game.

“I wanted to wear a Tottenham kit, but I don’t think that would’ve gone down well,” Kane said in response. Kane’s desire to improve also had roots in his admiration for Tom Brady, who he stumbled across while struggling to get into the Leicester team in 2013 — a spell when few could see him becoming a superstar for club and country.

Kane was sat at home watching NFL matches with increasing interest. One day in between games, he came across a documentary entitled “Mr 199”, detailing the story of how Brady was the 199th pick in his draft class.

“It was genuinely inspiring to me,” Kane revealed. “Brady believed in himself so much — and he just kept working and working, almost obsessively, in order to get better.”

Kane’s obsession with improving would be the driving force behind pushing for a move to Bayern last summer in order to ensure a career in which Tottenham and England’s record goal-scorer is not bereft of team trophies. Spurs had become top-four regulars and reached the 2019 Champions League final under Mauricio Pochettino, but progress had undeniably stalled in the four subsequent years. Bayern looked as close to a guarantee of silverware as anyone could get at the highest level.

There is, then, a considerable amount of schadenfreude in the red half of north London that Bayern look highly likely to lose the Bundesliga title for the first time in 12 years as Xabi Alonso’s Bayer Leverkusen hold a 16-point advantage with six games remaining.

Kane has scored 38 goals in 37 games across all competitions including six in eight Champions League matches. Despite Bayern’s wider malaise, he has maintained his own deadly form — 32 league goals is already a Bundesliga record for any player in his debut season and he has Robert Lewandowski‘s all-time high of 41 in a single campaign firmly in his sights.

But he will face arguably his sternest test in centre-back pairing William Saliba and Gabriel, who last week became the first defensive partnership to restrict Manchester City striker Erling Haaland to zero shots on target across both league games in a season.

Kane has played against them twice previously, scoring a penalty in a 3-1 defeat at Emirates Stadium in October 2022 before being shut out in a 2-0 home loss in January 2023’s reverse fixture.

Arsenal have evolved since then to become seemingly serial title challengers, but they have not been in the last eight of Europe’s premier club competition since 2010, having failed to qualify since 2017 and then suffering seven consecutive exits at the round-of-16 stage before that. Three of those defeats were to Bayern, who inflicted a 10-2 aggregate humiliation of the Gunners, winning both legs 5-1.

Sources told ESPN that those losses caused arguments within the squad at the time, with disagreements centering on some players believing others were failing to take responsibility in big moments. Arsenal were widely criticised for lacking leaders during this period and sources added that there were some players who privately agreed with that view.

Manager Mikel Arteta has generated a different feeling about Arsenal now. He was on the books as a player for five of those round-of-16 exits and witnessed first-hand how the glass ceiling formed and then hardened over his teammates.

Kane is not the only one motivated by past disappointment when Bayern face Arsenal this week.