Mikel Arteta suffered defeat in his first North London Derby as manager as Tottenham came from behind to claim victory.
With Spurs struggling, it seemed like a good time to play them and Alexandre Lacazette’s piledriver put Arsenal in control.
But individual errors are as common as attacking magic at Arsenal and a mix-up between Sead Kolašinac and David Luiz gifted Son Heung-Min an equaliser.
Arsenal missed a couple of chances and Pierre-Emerick Aubameyang smacked the post before Toby Alderweireld headed in the winner.
Arteta made just one change bringing in Nicolas Pépé for teenager Bukayo Saka. The Ivorian was brought in to add more of a clinical edge in the final third but a mis-controlled pass allowed Lucas Moura to play an inch-perfect ball to Harry Kane but Emi Martínez was alert enough to deny the England captain.
The Gunners then went up the other end and created a chance of their own. Héctor Bellerín showed glimpses of his former self to burst past two players and pick out Aubameyang but the forward couldn’t make a clean connection.
His strike partner Lacazette certainly got his connection right a few minutes later with a thunderbolt from just outside the area that flew into the top corner.
The attack displayed the best of Arsenal, but the defence displayed the worst. With no obvious options to pass forward, Kolašinac opted to knock it back to Luiz but his pass was too heavy and Son latched onto it before lifting the ball over Martínez.
The men in red struggled to replicate their scintillating attacking performance against Leicester and were given a warning when Ben Davies’ long range effort cannoned off the crossbar, with Martínez getting a slight touch.
That seemed to give Arsenal the boost they needed and after Pépé fizzed a shot wide Aubameyang went close from a free kick.
Granit Xhaka and Dani Ceballos started to control the midfield and after a period of sustained pressure Lacazette picked out Aubameyang in the box but the striker hit a venomous effort onto the woodwork.
Saka got his first taste of the North London Derby – for the first team at least – when he replaced Pépé with 20 minutes left.
Spurs weathered the storm and as Arsenal’s energy started to fade, the hosts found space in the back three. Martínez was called into action to deny Son and Kane but he could do nothing when a corner kick was glanced in by Alderweireld.
Arteta responded with a triple substitution that saw Joe Willock, Reiss Nelson and Cédric Soares introduced but they couldn’t salvage a point.