Nicolas Jackon's strike had the final say for Chelsea in one of the most chaotic derbies of the modern Premier League era.
Five disallowed goals, two red cards and a penalty summed up the night in which nine-man Tottenham fell to their first defeat of the season against former boss Mauricio Pochettino on his first return to Spurs since his 2019 sacking.
Dejan Kulusevski opened the scoring for Spurs who came out of the traps all guns blazing before a Cristian Romero red card and subsequent spot-kick dispatched by Cole Palmer turned the game on its head.
Destiny Udogie saw red in the second half with Spurs going down to nine, setting up Jackon to turn the game on its head and net a late hat-trick to secure all three points for Chelsea. Here are seven talking points from the derby.
1. VAR tries to make sense of the chaos
Four disallowed goals, a red and four yellow cards, a penalty, two goals, two serious injuries, handbags and a stray elbow - has there ever been a more chaotic first half than the one played out in north London on Monday?
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Son Heung-min suffered the first blow when his effort that would have put Spurs two ahead was ruled out for offside, but Tottenham were cruising at this point after Kulusevski's opener and very much on the front foot.
Destiny Udogie was then lucky not to have been sent off for a reckless two-footed challenge on Raheem Sterling before Romero kicked out at Colwill but also avoided seeing red. His luck would later run out after he was sent off for a lunge on Fernandez.
Nicolas Jackson netted a hat-trick for Chelsea (Getty Images)Sterling then saw a goal chalked off after he handled the ball in the build-up to the effort before his teammate Moises Caicedo saw the third strike of the match ruled out after Nicolas Jackson interfered with play from an offside position.
Jackon saw a fourth goal of the night ruled out for offside a little later before Pape Saar and Colwill engaged in some handbags that saw them both booked, despite the Chelsea man being the aggressor after a seemingly innocuous collision.
The final VAR check of the half came when Reece James caught Udogie with an elbow, but the referee didn't deem the contact violent and the right-back was allowed to continue.
Amid all the carnage, Spurs also lost James Maddison through injury after the Englishman pulled up off the ball. Van de Ven pulled his hamstring moments later and was also forced to make way, leaving Tottenham without either starting centre-backs.
Got all that?! Well, good, because things didn't exactly improve after the break after Udogie picked up a second yellow and was given his marching orders and Eric Dier later scored a goal out of nowhere that was also ruled offside.
VAR was without a doubt overworked in the opening 45 minutes and the flow of the match was regularly disrupted as a result, but after some high-profile clangers in recent weeks, and despite testing conditions, the officiating was largely up to scratch.
2. A tale of two Spurs defenders
It's fair to say Udogie and Romero understood the importance of the fixture - it's no secret Tottenham fans consider the Chelsea match to be up there with their derby with Arsenal.
But in being so fired up - too fired up - for the match they undid everything Postecoglou expertly drew up in the tactics room during the week and, ultimately, let their team down.
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Udogie's out-of-control lunge to dispossess Sterling could have ended in tears for everyone involved if it wasn't for the ex-Manchester City winger acknowledging the danger and removing his body from the firing line. The VAR check was arguably kind to the defender who could have easily walked on another day.
Cristian Romero was shown a red card (GEORGE BECK/PPAUK/REX/Shutterstock)Keen to be involved in the chaos, Romero, who was clattered by Thiago Silva only moments after the Udogie foul, kicked out at Colwill David Beckham-style, with VAR taking a look at the incident.
Somehow, the Argentine avoided being sent off for the moment of petulance, but his time would come a little later in the match when he recklessly fouled Enzo in the build-up to Caicedo's ruled-out strike.
A long VAR check ensued before Romero was correctly given his marching orders with Chelsea being awarded a spot kick, which Palmer was fortunate to dispatch.
Tottenham boss Postecoglou's half-time team talk would have no doubt involved him calming his players down, but Udogie still had one moment of madness left in him after the break and picked up a second yellow to see Spurs go down to nine.
3. A rollercoaster night for Maddison
Joe Cole called James Maddison the "signing of the summer" only two months ago, and the former Leicester City midfielder again showed why he's stealing the plaudits this season with a sensational ball to put Tottenham in the driving seat on Monday.
Now, Fantasy Football addicts will be quick to point out you get no points for the pass before the assist, but without Maddison's ball Spurs wouldn't have enjoyed the electric start they did in north London.
James Maddison went off injured for Tottenham (AP)Picking the ball up on the left, the Englishman sprayed his pass out right - spreading the play and catching the entire Chelsea team asleep in the process. He found Pape Saar who quickly played in Kulusevski to score.
But despite his night starting off so brightly, Maddison went down injured off the ball and had to make way. His absence - alongside the absence of Romero and Udogie - marked the end of Spurs doing anything creative and it's because of that Tottenham will be hoping the midfielder makes a speedy return.
4. Cole Palmer is ice cold from the spot
A lot was made of the former Man City star taking the ball from Sterling and demanding he take the penalty in Chelsea's recent 1-1 draw with Arsenal.
Some suggested the youngster should have had more respect for his senior teammate while others claimed Palmer was showing the right attitude to go far in the game.
He backed up his confidence by sticking the ball in the back of the net against the Gunners and then he matched that feat by burying his spot-kick against Spurs.
Cole Palmer netted for Chelsea (Getty Images)Guglielmo Vicario was without a doubt Tottenham's man of the match on Monday and he did well to guess correctly and get a hand on the spot-kick. But the power of Palmer's shot saw it hit the back of the net.
Interestingly, there didn't appear to be any kind of debate as to who would take this particular penalty with Sterling apparently happy to let the young hot-shot take the responsibility.
5. Van de Ven injury could be huge
Losing a first-team player is always a worry for a club gunning for the title - even if unexpectedly - but the injury alongside Romero and Udogie picking up suspensions could be huge for Spurs.
Micky van de Ven pulled up while tracking back and immediately reached for his hamstring while screaming in pain. It was never an option that he'd stay on the pitch and even had to be helped to the sidelines.
Micky van de Ven suffered a hamstring injury (AFP via Getty Images)There's no telling how long the defender will be out of action, but not for the first time on Monday the injury will leave Postecoglou ruing his luck with games against Wolves and Aston Villa on the horizon.
6. Jackon convinces after slow start
Chelsea played most of the second half against nine men of Spurs and, understandably, enjoyed most of the possession - but Pochettino's side were wasteful.
Jackson had a number of opportunities to put the ball in the back of the net and despite the heroics of Vicario should have been more clinical in the final third.
Pochettino grew increasingly frustrated watching the action from the sidelines, especially as Mykhailo Mudryk added to Chelsea's largely poor attacking play.
But Jackson eventually got his breakthrough when he tapped home from close range, latching onto the end of a sideways pass from Sterling, who was arguably Chelsea's player of the night.
He netted his second on the break after Son came close to equalising for Spurs - the effort was a carbon copy of his first, a close-range tap-in from a pass from his right. And then bagged his hat-trick with the game petering out.
7. Vicario is single saving grace
It was an incredibly tough night for the Spurs players who remained on the pitch on Monday - of the XI that started the derby only FOUR were still on the pitch when the final whistle sounded.
And while no one exactly covered themself in glory, Vicario was excellent for Tottenham and, initially, kept the scoreline respectable with a series of sensational saves to frustrate Chelsea.
As the game wore on and Chelsea failed to take their chances, Spurs went for broke in a bid to get something from the game.
They came close with Dier hitting the back of the net before the goal was ruled out and Son drawing a save from Robert Sanchez but became too stretched in the process.
As a result of the incredibly high line, Vicario was left exposed at the back and there was very little he could do about stopping Jackson.
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