When can Harry Kane break Jimmy Greaves' Tottenham record?

When Jimmy Greaves scored the last of his 266 goals for Tottenham Hotspur in 1970, he had racked up 58 more than Bobby Smith, the next most prolific player in the club's history.

However, he wasn't entirely satisfied with his final haul. "If I'd scored every goal I should have scored and missed," he later mused, "and missed every one I did score, my record would have been the best in history by far."

Greaves has stood out on his own for 53 years but Harry Kane has been clawing his way towards the legendary figure with an unrelenting scoring rate his predecessor would admire (and probably have a sly comment about as well).

A typically crisp finish to decide Tottenham's FA Cup third-round tie against Portsmouth took Kane to 265 goals with a cockerel on his chest. With the outright record just two goals away here's when and where Kane could lay claim to being the greatest goalscorer in Tottenham's history.

• Tottenham 1-0 Portsmouth: Player ratings as Spurs reach FA Cup round four
• Harry Kane sets up date with Tottenham destiny ahead of Arsenal showdown

15 January 2023 - Tottenham vs Arsenal

Aside from a final, there is perhaps no better stage for Kane to make Tottenham history than the impending north London derby.

As a former Arsenal academy player, Kane was released because he "was a bit chubby" and "wasn’t very athletic" according to Liam Brady, who was in charge of the Gunners' youth system at the time.

Not that Kane needs any more motivation to find the net against Arsenal - the 29-year-old is the all-time top scorer in the century-plus history of the derby.

19 January 2023 - Manchester City vs Tottenham

If Kane can't overtake Greaves against the Gunners, he won't have long to wait before another fitting setting presents itself.

Not only does Tottenham's trip to the Etihad Stadium represent a head-to-head with the reigning Premier League champions, but Kane has a muddy past with Manchester City. Tottenham's vice-captain spent so much of the summer of 2021 batting his eyelids in City's direction that it temporarily tainted his previously saintly status among some Tottenham fans.

By the time Spurs finished their meeting with City at the Etihad in February, Kane was very much back in the good books. In the dying embers of a bonkers match, Kane completed his brace with a 95th-minute winner to remind Pep Guardiola of what he missed out on.

23 January 2023 - Fulham vs Tottenham

While Fulham don't inspire the same fierce hatred in the Tottenham fanbase compared to other London rivals (see above), any team from the capital represents a favourable foe for Kane.

The Walthamstow-born striker has scored an unrivalled 45 Premier League goals against opposition based in London (including four against Fulham), overtaking the tally set by Arsenal icon Thierry Henry in October's derby against the Gunners.

5 February 2023 - Tottenham vs Manchester City

If at first you don't succeed, try, try again - a motto Kane has upheld throughout a career which didn't catch light until he was already 21. Should Kane fail to scrawl his name in the history books at the Etihad, City travel south two and a half weeks later.

Having been denied a move to Manchester in 2021, Kane was left out of the squad entirely when City venture down to north London that August. After a failed pursuit of Tottenham's scorer extraordinaire, City turned their attention to another goal-greedy frontman seven years younger than Kane this summer.

A clash with the only player to score more Premier League goals than Kane this season - Erling Haaland - adds another layer of narrative to this mouthwatering onion of a tie.

11 February 2023 - Leicester City vs Tottenham

If Kane is still trailing Greaves by the weekend before Valentine's Day, the fixture computer has gifted him a golden chance to seal the record against his favourite opponents.

Across 19 career meetings with Leicester, Kane has scored a sickening 20 goals - including a four-goal haul at the King Power Stadium in 2017.

Kane's prolificacy against the Foxes may be borne out of (a hint of) familiarity. During a three-month loan spell with the Midlanders in 2013, a 20-year-old Kane was afforded just five starts.

While wistfully watching on from Leicester's bench, getting anywhere near the scoring record Greaves set at Tottenham would have been outlandish even for Kane's daydreams. In the coming weeks, Kane will almost certainly have usurped the great man.