A late hat-trick from Nicolas Jackson fired Mauricio Pochettino's side to a victory in North London, as the Argentinian manager leaves familiar territory with all three points tucked under his sleeve.
It was the hosts who started off on top and they took the lead via a deflection from a Dejan Kulusevski shot after just six minutes. It wasn't long until they had the ball in the net once more, however the offside flag denied Heung-Min Son a ninth goal of the season.
It was then Chelsea's turn to ramp up the pressure. Destiny Uodgie and Cristian Romero both avoided a red card, before Raheem, Sterling had the ball in the back of the net. After a VAR review, the goal was chalked off for a handball.
The Blues then thought they'd taken the lead when Moises Caicedo found the bottom corner with a peach of an effort from outside the box, that goal was also chalked off - this time Jackson in the line of Guglielmo Vicario's vision.
However, in the process, VAR looked back at an earlier incident for a foul by Cristian Romero. His follow through was deemed worthy of a red card by Michael Oliver, who was sent for an on-field review, with Cole Palmer dispatching the penalty. The entire check lasted a total of eight minutes.
Spurs' troubles didn't end there. After Reece James was lucky to escape a straight red card at the end of the first half, it was Destiny Udogie's turn to make an unnecessary lunging tackle. Already on a yellow, he was sent off by Oliver and Spurs were reduced to nine.
Eric Dier thought he had equalised at the death, only to see his superb volley was chalked off for an offside in the build-up. Son also came close to equalising in added time before the late capitulation occurred...Two goals from Jackson saw him secure a hat-trick and a resounding victory for Chelsea.
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Romero cannot be a leader for Tottenham
Despite having a great start to the season, tonight proved why any Tottenham fan with doubts regarding the decision to appoint Cristian Romero to the leadership team were right.
Known for his aggressive defending, it was the Argentine's petulance and silliness that ultimately cost Tottenham on Monday night. Romero was lucky to escape red after he kicked out at Levi Colwill earlier in the half, before he was punished after a late follow through on Enzo Fernandez inside the Tottenham penalty area.
Some will argue that it wasn't meant, and that he actually won the ball first, however, it is nothing but nonsense to dive into a challenge like that, with studs showing, let alone inside the penalty area.
We believe that Michael Oliver made the correct call here, and the Argentine deserved his sending off - which will massively affect Tottenham who lost Micky van de Ven to what looked like a severe hamstring injury towards the end of the first half.
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VAR is not fit for purpose
Now, some may argue that this isn't a new thing, but tonight was a brand new, all-time low for VAR. Its also worth pointing out that this isn't anti-Michael Oliver, it is solely anti-VAR.
There was nine, yes nine, different checks on incidents inside the first half - this is totally acceptable, especially considering the ball was in the back of the net on six occasions. However, no check had a quick resolution.
There was an eight, yes eight, minute wait for a check on three different incidents in the same passage of play. Firstly, whether or not Jackson was in the line of sight of Vicario when Caicedo took the shot, and secondly to figure out whether Cristian Romero was to be penalised for a foul and then possibly serious foul play on Enzo Fernandez.
It took seven minutes before Michael Oliver was sent to the screen for an on-field review to judge whether he should send off Tottenham's Argentinian centre back.
Destiny Udogie and Chelsea's Reece James also escaped early baths for a studs-up tackle and elbow respectively.
We ask for 100% accuracy, but we also need some kind of efficiency in the process.
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Chelsea lack that cutting edge up front
Now, you may be thinking this is slightly odd considering The Blues scored four times at the Tottenham Hotspur Stadium in front of Sky Sports cameras on Monday night, but it wasn't as straightforward as you think.
Guglielmo Vicario had to pick the ball out of his net on seven occasions last night, yet was still The Lilywhites' man of the match, but that was partly down to Chelsea's lack of quality in the final third.
The visitors had a total of seventeen shots, only registering eight on target as they missed a hatful of clear-cut chances.
Nicolas Jackson scored a hat-trick on enemy soil, yet his only other goals this term have come against struggling Luton and Burnley and its safe to say he certainly hasn't lived up to expectations since joining from Villarreal for £32m in the summer window.
The main source of goals at this current time is coming from fellow youngster Cole Palmer, who has scored three times in the league from a deeper role than the Senegalese striker.
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Postecoglou's stubbornness could have cost Tottenham
Now, there's absolutely no point denying that the red cards to both Cristian Romero and Destiny Udogie cost Tottenham the game, but Ange Postecoglou's tactical stubbornness could have been a major factor in Spurs' late downfall.
The Australian has had the best ever start to a Premier League season for a new manager in the league, winning eight and drawing two tonight, however his unbeaten home record, stretching all the way back to November 2020, was abruptly ended against bitter rivals.
When Micky van de Ven came off injured, and his side dropped down to nine men, the former Celtic boss continued to deploy the high line, which has seen the Dutch centre back excel this season and even earn himself a first call up to the senior Netherlands squad.
With Eric Dier and Pierre-Emile Hojbjerg the pairing who ended the game, the arrogance from Postecoglou to not come away from his normal high line system was going to prove costly at one point, and it did, with Chelsea scoring three identical goals - it could have been even more had The Blues' attackers kept themselves onside.
The Tottenham boss said that "even with five men, we'll still have a go" during his post-match media duties, but if Spurs are to pick up a result at the weekend when they travel to Wolverhampton Wanderers in the early kick off, they may need to rethink their high-line approach with three regular defenders all guaranteed to be missing in action.
