Nine-men Tottenham suffered their first loss of the Premier League campaign in a fiery 2-1 defeat at home to Chelsea.
Jackson rifled in a 75th minute winner from Raheem Sterling’s square-ball pass as the Blues came from behind to win at manager – Mauricio Pochettino’s former home ground – with the Argentinean having managed Spurs between 2014-19.
The Senegal forward then struck twice in injury time to claim his first hat-trick as a Chelsea player and wrap up a clinical victory.
Dejan Kulusevski had earlier put Tottenham ahead in the sixth minute but Cole Palmer equalised from a 35th minute penalty, after Cristian Romero had been red carded for a foul on Enzo Fernandez.
The hosts’ disastrous evening worsened with injuries to Mickey van de Ven and James Maddison, whilst Destiny Udogie was sent off in the 55th minute for a second bookable offence.
Speaking to BBC post-match, Tottenham manager, Ange Postecoglou said: “There was a fair bit going on, a lot of VAR intervention, a hard game for me to analyse but I am very proud of the players. Right to the end they were trying to create something for us.
“The players couldn’t give any more than they did, part of this game is will, effort and determination and they showed that.”
Tottenham now sit second in the table, whilst Chelsea’s win lifted them up to tenth on goal difference from fellow London rivals, Crystal Palace.
Having slipped to second in the table over the weekend, Tottenham started with high energy and fluidity which saw Pape Matar Sarr play Son Heung-min through in the fifth minute, but the South Korea international saw his shot saved by Robert Sanchez.
That chance proved to be an early warning which Chelsea failed to heed as Sarr flicked on a sixth-minute diagonal pass for Kulusevski, who calmly rifled into the near-right corner to put Tottenham back top of the table at that point.
Pedro Porro almost doubled Spurs’ lead a minute later as he rifled upon goal from Kulusevski’s pullback pass of Brennan Johnson’s cross, yet Sanchez was able to make a comfortable save.
Chelsea’s first chance eventually came in the 11th minute as Jackson forced a save from Guglielmo Vicario, before Son briefly extended the hosts lead two minutes later with a tap-in but he was ruled offside via his right shoulder position.
Tottenham soon afterwards began to lose their composure and Romero was lucky not to be sent off in the 21st minute, after he retaliated with a kick on Levi Colwill following an initial shove on the Argentinean.
Sterling meanwhile scored for Chelsea amidst that incident seconds later but his goal was ruled out for handball, after his first shot rebounded off Porro onto his right arm before he put the ball away beyond Vicario.
Sterling though had found himself the subject of a reckless tackle from Udogie two minutes earlier, with the Italian getting away with a yellow card.
Fernandez and Thiago Silva then saw shots go wide for Chelsea but tensions soon hit boiling point in the 28th minute, as Moises Caicedo had an equalising goal disallowd due to Jackson interfering with play as the Colombian delivered his shot upon goal.
Romero meanwhile clipped Fernandez inside the box with a high-footed challenge which sent his compatriot to ground, and resulted in a red card for the Spus defender following a lengthy VAR review and referee – Michael Oliver awarded Chelsea a penalty.
Palmer eventually stepped up in the 35th minute and Vicario got a touch on the Englishman’s penalty, yet could only deflect it onto the right post, which saw the ball ricochet into the bottom-right corner to pull the West London visitors level.
Chelsea quickly pushed on after their equaliser against an imploding Spurs defence but failed to find a breakthrough goal before half-time, whilst the hosts lost Romero’s central defensive teammate – Mickey van de Ven to injury alongside James Maddison in two huge blows.
Tottenham however were lucky to not be down to nine men at the break after Sarr and Colwill came to blows in the tenth minute of injury time, yet Oliver decided to just yellow card both players than send either player off.
Reece James was then lucky not to be dismissed for Chelsea in the 11th minute of injury-time after he elbowed Udogie in the face, yet VAR deemed it a simple incident and not a yellow or red card offence.
Colwill though found himself hooked off at half-time by Mauricio Pochettino for Marc Cucurella, due to his ill-tempered first-half antics.
Upon the restart, Chelsea quickly made their one-man advantage count but their recurring end product issues reared its head, as Palmer rifled wide in the 47th minute in a fast start from the Blues.
Sterling then broke forward seven minutes later but his shot was blocked by Vicario, before he seconds later broke forward on a counter-attack, which drew a foul from Udogie who was consequently dismissed to put Spurs down to nine men with 35 minutes left on the clock.
If Chelsea thought that decision boosted their prospects of a second goal then poor finishing looked to be their Achilles heel, as Jackson flicked over the bar from James’ cutback pass following a short free-kick.
Jackson continued to push for his third goal of the campaign but his 58th minute shot was punched away by Vicario, when then blocked Palmer’s rebound shot.
Chelsea continued to press and eventually got their reward as Sterling broke forward up the right flank at the start of the 75th minute, and found Jackson unmarked to rifle his pass into the left corner to put the Blues ahead at Pochettino’s former team.
Tottenham however seemingly responded three minutes later as substitute, Rodrigo Bentancur flicked a free-kick behind for Eric Dier to volley into the top-left corner, but he was adjudged offside as Bentancur nodded the ball into his path.
Chelsea eventually clung on for a fourth league win of the season after Bentancur narrowly put a 86th minute header wide, as Spurs valiantly tried to chase an unsuccessful equaliser in which Son saw a 93rd minute shot denied by Sanchez.
Jackson subsequently rounded off Tottenham’s nightmare evening a minute later as he turned Gallagher’s pass into the net to seal a triumphant return to North London for Pochettino and his Blues, before he completed his hat-trick two minutes later.
The 22 year-old first turned in Connor Gallagaher’s 94th minute pass followed by a clinical strike from Palmer’s pass in the 97th minute, which secured Jackson his first Premier League hat-trick of his career.
Postecoglou meanwhile suffered a first home defeat as a manager since he began his 52-match unbeaten home run in November 2020 during his time at Yokohama F. Marinos, then two-year spell at Celtic plus now Tottenham.
Tottenham continue their push for the Premier League title with a trip to Wolves on Saturday 11 November, with kick-off at Molineux set for 12:30pm GMT live on TNT Sport 1 in the UK.
Chelsea host Spurs’ title rivals, Manchester City on Sunday 12 November at 4:30pm at Stamford Bridge, live on Sky Sports in the UK.
Tottenham: Guglielmo Vicario, Pedro Porro, Cristian Romeero, Mickey van de Ven (Hojbjerg 45+1′), Destiny Udogie, Yves Bissouma, Pape Matar Sarr (Bentancur 61′), Dejan Kulusevski (Skipp 61′), James Maddison (Royal 45+1′), Brennan Johnson (Dier 34′), Son Heung-min
Substitutes: Oliver Skipp, Pierre-Emile Hojbjerg, Richarlison, Bryan Gil, Emerson Royal, Eric Dier, Giovani Lo Celso, Fraser Forster, Rodrigo Bentancur
Chelsea: Robert Sanchez, Reece James (Gusto 77′), Axel Disasi, Thiago Silva, Levi Colwill (Cucurella 45′), Moises Caicedo, Enzo Fernandez, Cole Palmer, Conor Gallagher, Raheem Sterling, Nicolas Jackson
Substitutes: Marc Cucurella, Benoit Badiashile, Mykhailo Mudryk, Noni Madueke, Lesley Ugochukwu, Malo Gusto, Dorde Petroivic, Ian Maatsen, Deivid Washington
Referee: Michael Oliver