As a lover of 'what if' moments, it's difficult not to look back upon that night against Chelsea as a defining crossroads in Tottenham Hotspur's modern history, as the Lilywhites slipped to a first Premier League defeat in Ange Postecoglou's 11th match at the helm.
Depleted following two red cards and a raft of injuries, the hosts creditably stood firm until the closing stages, having seen Eric Dier volley home what looked to be a remarkable equaliser on the 78-minute mark.
Alas, it was not to be, as Nicolas Jackson converted one of the least impressive hat-tricks going to seal a 4-1 win, halting Postecoglou's early momentum and potentially setting the wheels in motion for the decline that has followed.
Indeed, since that defeat back in November 2023, Spurs - who started the season unbeaten - have gone on to lose a further 49 league games, 16 of which have come in 2025/26.
Roberto De Zerbi, now two games into his Tottenham tenure, needs to stop the rot, and swiftly, to avoid this two-year slump reaching a new nadir.
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Igor Tudor chopped and changed, both in terms of personnel and in tactical set-up, although in De Zerbi's 4-3-3 or 4-2-3-1, there is a clear plan emerging, with Conor Gallagher leading the press in what was a high-octane performance from the home side at N17.
The Englishman, polarising he may be, appears set to be central to the Italian's approach based on these first two games, having hunted down Brighton and Hove Albion's Bart Verbruggen in one notable act at the weekend.
Gallagher is key, it would seem, and so too should be Xavi Simons, the Dutchman restored to the starting lineup and taking his chance with both hands, having teed up Pedro Porro for the game's opener, while rifling in what looked set to be the winner late on.
Criticism of his euphoric celebration, considering what followed in stoppage time, is to be expected, but such a reaction from the 22-year-old was understandable after a season in which he has been starved of consistent minutes under a succession of managers.
Positives too can also be seen in Antonin Kinsky's quietly calm performance again for the second weekend in a row, the Czech 'keeper shaking off his Madrid woes to emerge as one of the brightest performers of De Zerbi's tenure thus far.
Having missed much of 2026 thus far, Spurs evidently appear a better side with Rodrigo Bentancur in it, after failing to win without him, while lessons have also been learned with regard to those who weren't in the starting XI on Saturday.
The new Eric Dier could be on the periphery now under De Zerbi
Dier was denied his magic moment against the Blues, and was subsequently denied much of a role too under Postecoglou, departing in January 2024 after making only four Premier League appearances in the first half of the season.
Once a valued member of Mauricio Pochettino's youthful side, the England international had drifted toward liability territory in his latter Spurs days, notably making three errors and giving away two penalties in 2020/21.
A persistent issue was also the uncertainty over his best position, be it at right-back, defensive midfield, centre-back or part of a back three, as the now 32-year-old never truly nailed down a consistent role.
That appears to be an issue also plaguing compatriot Djed Spence in the current ranks, the former Nottingham Forest and Middlesbrough man having flitted between a variety of roles himself in his turbulent Tottenham career to date.
The £20m signing, to his credit, has overcome a peripheral start under Antonio Conte to emerge as a regular fixture since Postecoglou's time at the helm, even now in contention for a World Cup place despite the wealth of full-back options at Thomas Tuchel's disposal.
Hopes of heading to the United States might well be hampered by a quiet end to the campaign under De Zerbi, however, with Spence failing to start either of the last two games, as the new boss favoured a more conventional full-back pairing of Porro and Destiny Udogie.
Utilising the right-footer at left-back doesn't appear to be in the mind of De Zerbi, while that man Porro appears to suit the inverted, creative role that the former Marseille boss is keen on on the right.
Spence - who has also operated as a makeshift centre-back or as a winger this season - is perhaps suffering now from not nailing down either full-back role, left in something of flux just like Dier before him.
Equally too, there are questions to be asked of his defensive contribution - just like Dier - having been singled out by Sky Sports pundit Jamie Carragher against the Seagulls for ambling back in the build-up to Georginio Rutter's last-gasp equaliser:
"But Djed Spence, I don't like this. You've got to sprint back. He's walking. He was a sub. He's only been on 15 minutes."
Considering the 25-year-old hasn't even scored or assisted either in the top-flight, it's hard to see what he's offering in either direction, putting his long-term future into doubt under De Zerbi.
Having seen one Italian manager over look him at the start of his time in north London, another could now bring it to a conclusion.