Arsenal's traumatic start to the season continued as Tottenham won the north London derby to leave their arch-rivals languishing two points above the Barclays Premier League drop zone.
Spurs underlined their new-found status as the second best side in the capital thanks to Kyle Walker's first goal for the club 17 minutes from time.
Aaron Ramsey cancelled out Rafael van der Vaart's controversial first-half opener but the first match of Arsene Wenger's 16th year in charge of the Gunners ended in another defeat, maintaining the pressure on the beleaguered Frenchman
Arsenal duo Theo Walcott and Gervinho were both passed fit for today's north London derby against Tottenham at White Hart Lane.
Both recovered from respective knee and hamstring problems as the Gunners made one change from the side that beat Bolton in their last Barclays Premier League outing, with Francis Coquelin coming in for the injured Laurent Koscielny.
Tottenham striker Emmanuel Adebayor started against his former club as the home side also made one change from their previous league game, Jermain Defoe coming in for Sandro in a more attacking formation.
Today's match was Arsene Wenger's first of his 16th year in charge of Arsenal, but the Frenchman may not have felt much like celebrating that incredible milestone in the midst of the most testing period of his tenure.
Despite the Gunners having recorded three straight wins in all competitions following their worst start to a league season for 58 years, they still looked extremely vulnerable.
Indeed, Spurs began the derby as favourites for the first time in Premier League history after shaking off their own poor start in some style.
It appeared ominous for Arsenal when their defence was exposed three times in the first seven minutes. Defoe nodded over a difficult header and Adebayor was just unable to keep the ball in play after getting round the back.
Wojciech Szczesny then came to the rescue one-on-one with Scott Parker after makeshift centre-back Alex Song surrendered the ball.
The visitors weathered the storm and Walcott saw a shot deflected inches wide as they began to assume some semblance of control.
But Tottenham were pouncing on every error and Gareth Bale's cross was just too far behind Rafael van der Vaart for the Dutchman to steer on target.
Van der Vaart picked up the game's first booking for clattering into Kieran Gibbs but almost broke the deadlock in the 28th minute when his flick from Defoe's cross was saved by Szczesny.
Arsenal surged down the other end and Robin van Persie beat Younes Kaboul and got to the byline before putting the ball on a plate for Gervinho, who somehow fired wide.
It was a glorious chance and they might have been made to pay when Per Mertesacker was carded for tripping Defoe, but Van der Vaart's free-kick hit the wall.
Walcott curled over from 20 yards as the Gunners continued to enjoy more of the ball but their old weakness of trying to walk it in surfaced.
And all their good work was undone when Tottenham took the lead with a controversial goal five minutes before half-time.
Defoe and Adebayor were the creators, the latter's ball finding Van der Vaart, who appeared to control the ball with his arm before slotting it past Szczesny.
The Holland star also ran into the crowd to celebrate but escaped a second booking.
There was still time for Bale to go close with a 30-yard screamer and Aaron Ramsey to see a shot deflect straight through to Brad Friedel.
Van der Vaart's goal was Spurs' 10,000th in competitive football and they set about trying to make it 10,001 after the restart, Luka Modric mishitting his shot from a short corner.
The marauding Bale also drilled narrowly over, while at the other end a mix-up between Van Persie and Ramsey saw a good chance go begging.
Ramsey made amends in the 51st minute after Spurs completely switched off, allowing Song to pick up Kaboul's clearance, bound down the left and cross for the Wales captain to turn home.
It was all Arsenal, for whom Coquelin was having a fine game on what was his first Premier League start since the 8-2 mauling at Manchester United.
But they still looked vulnerable every time Spurs attacked and Adebayor wasted a glorious one-on-one with Szczesny when he sidefooted Bale's pass too close to the keeper.
Van der Vaart, who seemed to be carrying an injury, was withdrawn for Sandro just past the hour mark and he was soon followed by Bacary Sagna.
The right-back landed awkwardly on his right ankle and was taken off on a stretcher to be replaced by Carl Jenkinson for the final quarter.
Yossi Benayoun then came on for Walcott for the final 19 minutes but Arsenal fell behind again a minute later.
The ball fell to Kyle Walker 35 yards out and he was allowed to advance 10 yards before unleashing a swerving low drive that Szczesny got hands to and really should have kept out.
Bale wasted a golden chance to kill the contest when the visitors completely failed to deal with a long ball which the winger struck wide.
But Bale hit top gear to skin Jenkinson before crossing for Defoe to force an acrobatic save from Szczesny.
Adebayor limped off to be replaced by Jake Livermore before Vedran Corluka came on for Parker in stoppage-time as Tottenham went close to a third goal on more than one occasion.
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