Chelsea missed a golden opportunity to close the gap at the top of the Barclays Premier League as Luka Modric's winner helped inflict Guus Hiddink's first defeat since arriving in England.
A suspect vehicle near White Hart Lane delayed kick-off, meaning the visitors kicked off knowing leaders Manchester United were struggling at Fulham, but they failed to take advantage.
Victory would have taken them within a point of United but Hiddink's men were frustrated by a Tottenham side who have been transformed since Harry Redknapp's arrival five months ago, with Modric striking the winner just after the interval.
Spurs goalkeeper Heurelho Gomes also played a huge part in the victory, saving from John Terry late on when the away fans thought they were on level terms. Alex also hit the crossbar in stoppage time as Spurs held on.
Redknapp's men were relegation candidates when he took over in October but they are unbeaten in six league games and could be in with a shout for Europe.
On a personal level, Redknapp had not beaten Chelsea in a league game since 1999. More importantly, he feels his side could challenge the traditional top four in their next campaign.
The visitors, however, have still not recorded a win over one of their London rivals this season and their task was not made easier by Ricardo Carvalho picking up an ankle injury this week, meaning Alex deputised at centre-back.
Deco's hamstring problem meant Juliano Belletti came in on the right side of a midfield squeezed for space, especially when Spurs skipper Robbie Keane dropped back to help his team-mates.
Hiddink's men were predictably limited to long shots and Michael Essien, back from a serious injury, forced Gomes into a save which he gathered at the second attempt early on.
At the other end, Jermaine Jenas just cleared the angle of crossbar and near post with a fizzing drive.
The hosts got closer in the 18th minute after Alex failed to deal with a long punt forward, with Petr Cech required to beat away Keane's powerful volley.
Cech stopped Keane again after Vedran Corluka had raced down the right and pulled the ball back, although this effort was much closer to the Chelsea goalkeeper.
The visitors were being denied space on the ball, with Nicolas Anelka often dropping into midfield to get involved. That was how the France striker started the move that ended with the ball breaking to him on the edge of the area and Gomes saving at the near post.
Encouraged by Chelsea's limited chances, Spurs attempted to break forward. Cech claimed the ball when Keane cut in and had a shot blocked by Alex and the Chelsea goalkeeper also plucked the ball from under his crossbar from Ledley King's looping header.
King clattered Didier Drogba with his thigh while winning a header and the Chelsea striker looked dazed while receiving treatment and heading down the tunnel, the visitors seeing out the first half with 10 men.
Drogba was fit to start the second half but Chelsea were behind within five minutes of the restart.
Aaron Lennon received the ball on the right, feigned to go down the flank but instead he crossed early, between Ashley Cole and Frank Lampard.
Keane could have struck but Modric took control of the situation, crisply finishing from the edge of the area into the bottom corner for his fourth goal of the season.
He almost repeated the trick when he got on the end of another Lennon cross, but this time his effort lacked power.
Hiddink's response was to bring on Ricardo Quaresma for Belletti, moments before Lampard struck the frame of the goal with a header at the far post.
Gomes saved from Drogba at the near post and from Quaresma's long-range effort as Chelsea searched for the equaliser.
Drogba sliced another shot wide, with Hiddink's next move to bring on Florent Malouda for Essien.
Terry forced Gomes into his stunning full-stretch save, then King's block on Anelka was equally important. Alex hit the bar deep in injury-time with a header from a corner but Spurs held on.