Losing to Chelsea always hurts but, for all their spirit, bravery and fight, nine-man Spurs were the makers of their own downfall as their unbeaten start to the season was ended by their former head coach, Mauricio Pochettino, whose side eventually won 4-1.
It is genuinely difficult to know where to start in assessing a game including no fewer than five disallowed goals (three for Chelsea, two for Spurs; four for fractional offsides, one for a handball), two red cards for the hosts, two stoppage-time goals and a nasty injury to Micky van de Ven - which, long-term, might be the most damaging incident of the lot.
The bottom line, however, is that Spurs threw away control of the game at 1-0 up, and perhaps with it their brilliant start under Postecoglou. The Australian will look at the positives and his side undoubtedly showed enormous character.
At 2-1 down - after Nicolas Jackson had finally scored to put Chelsea in front with the first of his three goals - Spurs nearly equalised three times, despite being two men down.
Eric Dier had a goal ruled out, Rodrigo Bentancur missed from close range and Heung-min Son forced a smart save from Robert Sanchez moments before Jackson's second and Chelsea's third made it 3-1.
Instead of leaving the ground, most of the home fans rose to give Spurs a standing ovation in a genuinely uplifting moment. Postecoglou, however, will be left frustrated.
His side were leading through Dejan Kulusevski's deflected strike when Son scored the first of four disallowed goals in the first half - ruled out for a marginal offside.
That would have made it 2-0 to Spurs and, at that point, they were heading back to the top of the table and piling the pressure on the returning Pochettino.
From there, Spurs lost their heads, allowing the game to quickly descend into a scrap with an energy reminiscent of Pochettino's most infamous previous game in this fixture, the Battle of the Bridge in May 2016.
Cristian Romero was particularly guilty and the Argentine was sent off in the 33rd minute for a dangerous follow-through on his international team-mate Enzo Fernandez in the box.
Destiny Udogie, who started the chaos when he was lucky not to earn a straight red for a two-footed lunge on Raheem Sterling, followed for an early bath in the 55th minute after another lunge on the winger - leaving Spurs with an enormous challenge.
Romero was shown his straight red card following a series of VAR checks, which chalked off Moises Caicedo's equaliser for a tight offside call but awarded Chelsea a penalty, which was converted by Cole Palmer to level the score.
Earlier, Romero had been lucky to avoid a VAR check for a petulant kick off the ball on Levi Colwill which was not checked as the VAR seemingly focussed on disallowing Chelsea's first equaliser for a Sterling handball.
Romero will likely get a three-match ban, ruling him out of the game against Manchester City and Spurs will surely be without their other centre-back for an extended period, too, after Van de Ven pulled up with a serious-looking hamstring injury.
If he is sidelined for an extended period, it would be an enormous blow.
Subs Dier, Emerson Royal, Pierre-Emile Hojbjerg, Oliver Skipp and Bentancur all did their bit for Spurs in the second half as the hosts fought valiantly, but they will be a lesser team without their stars.
James Maddison, too, was forced before the interval after appearing to turn his ankle, although he appeared to want to continue and it may have been a tactical or precautionary change.
Postecoglou will be proud of his players' fight and the way they stuck bravely to his high defensive line in the second half, even if it cost them in the end.
But this was a night when Spurs' were naive and paid the price.