He himself had a fine year, bagging 30 goals in 38 Premier League games. It was his first season without any major injuries, and he is the first player in the league's history to hit the 30-goal mark in two separate seasons.
But many argue that he needs to win something - anything - to cement his legacy as one of the game's greats.
Individual accolades had flowed easily - this season Kane broke numerous records for club and country, most notably becoming both England and Tottenham's all-time leading goalscorer.
He is seemingly just two or three seasons from reaching Alan Shearer's all-time Premier League goalscoring record of 260 (Kane currently has 213). However, Tottenham's reluctance to sell to a domestic rival may see him forced to give up that chase - at least temporarily - to win trophies abroad, as Spurs face up to another frustrating period of transition.
Kane has never been a stranger to transfer speculation. His numbers are well-documented, his unique finisher-meets-playmaker style much revered, and his leadership and drive highly valued by both his club and national team.
Manchester City's failed attempt
He seemingly came close to joining Manchester City in the summer of 2021, only for Guardiola to spend the money on Jack Grealish instead, and the following season they activated Erling Haaland's release clause to bring the Norwegian superstar to the Etihad. Any reports linking Kane with a move to City went ice cold.
This particular episode felt different to those that came before.
Those 'in the know' suggested Kane’s head had very much been turned and that he was pushing for the move. Tired of winning only individual accolades and hungry to be competing for football's highest honours - and with a pre-Haaland City desperate for a replacement for departing Sergio Aguero - the deal looked like it had some legs.
Several sticking points existed, though. Most notably a very fresh, lengthy and lucrative contract that was signed by Kane only a season prior, effectively allowing Tottenham to slap a bloated price tag on the player's head. It also cannot be understated the value of Kane's overall profile to the club.
Bayern have been keen before
The German giants even openly admitted to the Englishman being on their radar. Whether talks ever took place - or whether Spurs chairman Daniel Levy would have even entertained them - remains unknown.
The rumours were put to Harry Kane during a press conference ahead of Tottenham’s Champions League group stage tie against Eintracht Frankfurt back in October.
In a rare example of the player addressing the talk surrounding him, and sitting side-by-side with then-Spurs boss Antonio Conte, Kane was quick to dismiss the rumours, but not without passing on positive words for the German champions:
"I'm focusing on Tottenham Hotspur and (we're) trying to do our best," Kane said.
"For sure Bayern are a top, top club but all my concentration is on Tottenham."
Bayern Munich ultimately backed off, at least to a degree, stating they would likely make their move "next summer".
And now here we are, with a reported formal bid upwards of £60 million faxed through to Spurs - and the club reportedly prepared to bid higher.
More and more Brits abroad
While a part of Kane is undoubtedly disappointed to have missed out on the Manchester City move, the Bayern links pose some interesting questions.
As more and more English stars make their way to clubs across Europe, the Bundesliga has proven to be an excellent breeding ground for young English talent, notably in the development of Jadon Sancho and Jude Bellingham.
Sancho of course eventually secured his big-money move away to United with mixed reviews, while Birmingham-born Bellingham has recently secured a headline-grabbing transfer to Real Madrid and no doubt has a hugely successful career ahead of him.
There are also those outside of England and Germany that are putting in notable performances at high-profile clubs. The likes of Chris Smalling, Tammy Abraham and Fikayo Tomori are all drawing huge plaudits in Italy and have all won major club honours in the last two seasons - more than Kane has won in his career.
Kane may well see it as a worthwhile endeavour to make the move to Bayern Munich, who are historically something of a cheat code when it comes to German football.
The odds would be strongly in his favour to win some silverware whilst there. But, potential Champions League success aside, and with the utmost respect to German football, are German medals enough for him when it comes to the end of his career, particularly when you've won them with a completely historically dominant Bayern?
The English public is much less likely to remember a club resume that features only Bundesliga or DFB-Pokal titles. Of course, a Champions League winners medal would take much more pride of place than his runners-up piece, but to uproot his family to Germany when he's an increasingly key figure in British culture now?
It may be a step too far from home comforts, and may not be quite what he was hoping to achieve.
There are also the much-talked-about Premier League records at stake.
Kane has long been touted as the man to break Alan Shearer's all-time scoring record of 260. Should he stay fit and in England for the foreseeable future, that record is very achievable.
Haaland's terrifying numbers could well make it short-lived, but that's another matter altogether. The question is, with such rare and palatable records on the table - would Kane really want to pack up and ruin his chances of a rare place in history?
From a tactical perspective, it doesn't take a footballing expert to suggest that Kane could play for any top team in the world.
Consistently putting up competitive goal tallies every year, his unique knack of being able to drop between the lines and provide assists for fellow attackers is a useful tool for any manager, and pacey forwards like Sadio Mane, Leroy Sane, Serge Gnabry and Kingsley Coman would be even more devastating with his additional supply line.
He's also a remarkably intelligent player with experience in the biggest games at both club and international levels, so (language barriers and culture aside) it's hard to see him struggling to adapt to life on the pitch in any league.
Daniel Levy's dilemma
The only other question remains: is there any realistic scenario where Spurs would sell arguably their greatest and most valuable asset in the club's history? Well, in short, the answer is 'yes'.
While they'd be reluctant, Tottenham would be far happier to see Kane go abroad than remain in the Premier League. This was a major sticking point in the failed City move - Daniel Levy is no longer in the market of strengthening clubs that he perceives to be "direct competitors".
Under pressure from fan groups to invest more on the pitch and often accused of putting profits before glory, Spurs will likely open the chequebook for Kane and his representatives to convince him to stay in north London.
But Kane has also suffered from injuries throughout his career, with particularly infamous issues with his ankles often causing him to miss chunks of the domestic season. Some doubts are cast over his longevity as an elite-level striker in the Premier League, renowned for its physicality and gruelling fixture list.
He is also entering the final year of his contract and can potentially leave for free at the end of next season.
There will come a point where, should an acceptable offer be received from the right club, Levy may be open to taking the exit strategy.
At the same time, coming off the back of such a terrible season in which many fans are already at the end of their tethers with the club's ownership, now is perhaps not the best time to be selling one of the best players your club has ever had.
Spurs fans will be hoping their hero remains one of their own for the remainder of his career, but should their barren trophy spell go on much longer it's hard to see how the club could stand in Kane's way.