Substitute Carlton Cole scored his first goal for Charlton to leave Tottenham in the relegation zone. Cole, on loan from Chelsea, glanced home a 69th minute header to break Spurs' hearts.
Tottenham dominated large spells of the game but paid a heavy price for failing to convert their superiority.
Charlton goalkeeper Dean Kiely produced two excellent first-half saves to leave Spurs pointless over Christmas.
Both teams went at it from the first whistle, with Johnnie Jackson rasping an early volley inches wide for Spurs.
Kiely then produced a great save to deny Robbie Keane after the Irishman had cutely swapped passes with Frederic Kanoute to open up the Charlton defence.
The Addicks then took up the pace, with Radostin Kishishev's powerful shot felling Gus Poyet before Spurs keeper Kasey Keller kept the scores level.
Paolo di Canio's pass sent Jonatan Johansson clear, and Keller spread himself to save and deserved his slice of luck when Johansson put the loose ball wide.
The action swung to the other end where Kanoute rose to meet Rohan Ricketts' cross only for Kiely to acrobatically tip over.
Spurs then began to dominate, and an intense spell of pressure penned Charlton into their own half.
But Tottenham were unable to convert their superiority into a goal.
Charlton asked questions of the Spurs defence at the start of the second half, but Tottenham continued to waste chances, with Mauricio Taricco firing wide after Keane's free-kick fell kindly for him.
Jackson was turning in an impressive performance and he and Ricketts teased in a series of enticing crosses but no white shirt got on the end of them.
Mark Fish justified his recall to the heart of the Charlton defence with a solid performance and he timed his tackle to perfection to halt Keane as he rampaged into the box.
Spurs' concern at their failure to convert chances was growing and they paid the price when Charlton took the lead on 69 minutes.
Paolo di Canio clipped a corner to the near post where half-time substitute Cole got in front of his marker to glance the ball home.
There was a swagger to Charlton's play and Di Canio's slick skills set up Scott Parker to curl a shot inches wide.
Cole was inches away from a second whe he lunged at Parker's free-kick driven across the box.
Spurs never looked like pulling a goal back, and as Charlton rose to fourth spot, Spurs dropped into the bottom three and were booed off the pitch.