Tottenham came back from a goal down to earn their first league win over Chelsea since 1990, thanks to an impressive goal from Aaron Lennon.
Lennon was superb for Tottenham
The visitors took the lead when Claude Makelele fired in a superb volley.
Michael Dawson brought Spurs back into the match with a well-placed header before Lennon capitalised on Robbie Keane's good work with a crisp finish.
Chelsea were reduced to 10 men when John Terry picked up a second booking over an incident with Pascal Chimbonda.
The result leaves the Blues three points behind Premiership leaders Manchester United.
However, both Chelsea and Tottenham produced some outstanding football on a chilly day under the floodlights of White Hart Lane.
Until midway though the first half it was Chelsea who played the champagne stuff, while Spurs - who had last beaten Chelsea at home in the league in 1987 - looked on enviously.
Paul Robinson's goal was under siege early in the half and Robben was guilty of not making the most of Spurs' fragility when he dallied on a through-ball, allowing Ledley King to make a vital interception.
The resulting corner was cleared but only as far as Makelele. The holding midfielder is not renowned as a potent threat to goal but, on this occasion, he connected beautifully with a volley from outside the area.
It left Chelsea manager Jose Mourinho grinning from ear to ear, most probably out of bemusement at having watched such a rare event.
The immediate aftermath saw the Blues tear Spurs apart, with Michael Ballack forcing a save from Robinson with a low, drilled free-kick before Frank Lampard made his England colleague tip over the bar following his stinging shot.
So when Dawson's goal came, it not only revived the home team's spirits but also swung the game their way.
Dimitar Berbatov, whose form has been as inconsistent as his side's after joining in the close season, almost put Tottenham into the lead but his mazy run and shot trickled just wide of Henrique Hilario's left-hand post.
And just before the break Lennon provided a stunning cross from the right that was met by Keane, who headed on to the top netting.
If the crowd thought the first half was eventful, then they had a treat in store in the second.
With seven minutes of the half gone, Keane dazzled substitute Khalid Boulahrouz, who came on for Paulo Ferreira, and fired in a great cross into the area that was controlled and then coolly finished by the diminutive Lennon.
It was fantastic technique from the England star and was just reward for his valiant work.
Chelsea began to look more desperate as Spurs grew in confidence and that anxiety resulted in fouls committed.
For the Blues this proved costly when Terry was shown his second yellow and sent off for what seemed like an altercation with Chimbonda.
Chelsea still pressed and were unlucky not to see Arjen Robben's curled effort fly in instead of rebound off Robinson's right-hand upright.
Frank Lampard and Salomon Kalou also went close but Spurs held on for a famous win.
Tottenham: Robinson, Chimbonda, Dawson, King, Assou-Ekotto, Lennon, Jenas, Zokora, Ghaly, Berbatov, Keane (Defoe 85).
Subs Not Used: Cerny, Davids, Mido, Huddlestone.
Booked: Dawson, Ghaly, King.
Goals: Dawson 25, Lennon 52.
Chelsea: Hilario, Paulo Ferreira (Boulahrouz 46), Ricardo Carvalho, Terry, Ashley Cole, Ballack, Makelele (Wright-Phillips 63), Lampard, Essien, Drogba, Robben, Boulahrouz (Kalou 68).
Subs Not Used: Cudicini, Joe Cole.
Sent Off: Terry (72).
Booked: Paulo Ferreira, Ashley Cole, Makelele, Terry, Ballack.
Goals: Makelele 15.
Ref: G Poll (Hertfordshire).