Harry Kane’s awkward Arsenal memory, Arsene Wenger’s anger and brutal Tottenham retort

Few players have given multiple Arsenal managers down the years the kind of headaches that Harry Kane did during his Tottenham days – next month, he returns as a Bayern Munich player

Harry Kane has been in sensational form for Bayern Munich this season (

Image: Getty Images)

“Harry Kane, he’s one of our own!”

It’s a chant that has been enjoyed both in earnest by Tottenham fans and sarcastically by Arsenal supporters keen to point out the fact that Spurs’ record goalscorer was once on the books of the Gunners and is a boyhood fan of the three-time Premier League winners.

Kane will soon be back in north London, though it will be the red half, as his Bayern Munich side have been drawn against his old enemies in the last eight of the Champions League. The England captain left Spurs in the summer to win the game’s biggest honours, but Arsenal are standing in his way to European success.

It’s unlikely that the striker will be welcomed back to the capital with open arms by the Emirates faithful. With that being said, Mirror Football has taken a look at the 30-year-old’s complicated relationship with Arsenal.

Awkward beginnings Harry Kane (bottom left) during his time in the Arsenal academy

During Kane’s four years as part of Arsenal’s academy set-up, the future Spurs talisman was so desperate to represent the Gunners he offered to go in goal. Former Arsenal assistant academy manager Roy Massey explained that the Gunners felt Kane wasn’t good enough to lead the line, but were willing to see how he fared between the sticks.

“When I see Harry now I can’t help but to think back to when he was a starry-eyed 12-year-old, sat with his mum and dad in my office as I told him he wasn’t quite up to the standard we were looking for,” Massey told Mirror Football last year. “That was the hardest part of the job, telling lads that Arsenal were letting them go.

“Next thing, Harry’s dad came back in and told me he now wants to be a goalkeeper – and I thought the least I could do was to send him to work with our ‘keeper coach Alex Welch.

“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. Some lads are lost to the game forever because they can’t get over the disappointment.”

Of course, much to the frustration of Arsenal fans everywhere, Kane did bounce back spectacularly. He went on to rewrite Spurs history, but the photo of the Three Lions skipper in his Gunners shirt celebrating the 2004 title triumph is never too hard to find on social media.

Spurs stardom Harry Kane often found the net against Arsenal (

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Getty Images)

As mentioned, Kane would go on to become the greatest goalscorer in Spurs history following Arsenal’s snub. Many of those goals came to the detriment of the Gunners, with the striker bagging 14 goals in 19 north London derbies across all competitions. In his last season at his former club, he scored at the Emirates during Spurs’ 3-1 defeat in October 2022.

Back in 2015, Wenger addressed the fact that he could have been Kane’s manager had the Gunners not parted ways too soon. He conceded he didn’t know whether to laugh or cry at the situation.

“I didn’t know, I read it in the papers,” Wenger admitted. “I found it quite funny, you know, and you are always a bit angry as well because I asked: ‘Why did he go?’ But at that age, boys can move here and there.”

The Frenchman always was known for his keen eye for talent and he certainly wasn’t wrong when he claimed: “He is a very interesting and very strong striker. He has top qualities and I think he will make a great career.”

Cutting all Arsenal ties Harry Kane as a boyhood Arsenal fan (

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Internet Unknown) Harry Kane scored 280 goals for Spurs (

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Getty Images)

Though Kane didn’t actually end up leaving Spurs until the summer of 2023, the summer of 2021 saw speculation surrounding his future reach fever pitch, with both Manchester clubs keen on his signature.

Kane was quick to make clear that one club he wouldn’t be interested in was of course Arsenal. The striker was quizzed by famous Gooner Piers Morgan over whether he has any regrets about his Arsenal career not working out, or whether he’d ever go back to the Emirates.

His reply was emphatic. “Well, I played for Arsenal when I was younger and unfortunately for them they let me go,” Kane explained. “I have been at Tottenham since I was 11 years old and I’m reaping the rewards of that now.”

Morgan asked: “Are you itching to go back to your roots?”, but Kane was having none of it as he hit back: “Absolutely not, no. [Tottenham are] in a good spot at the moment so I am happy.”

A final shot at revenge Harry Kane’s Bayern Munich side have drawn Arsenal in the Champions League (

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FC Bayern via Getty Images)

Kane doesn’t seem like someone to hold grudges, certainly not this long after leaving Arsenal as a boy. But when he rocks up at the Emirates with his Bayern Munich team-mates next month, he knows that he’ll have the entire Spurs fanbase also willing him on to a win.

He’s no stranger to scoring against the Gunners, but rarely has he had the support of two clubs trying to get him over the line in the process. With that being said, this is a stronger Arsenal outfit than any of the ones Kane faced during his Spurs days and a win won’t come easy in either leg.

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