Bolton recorded their first win at White Hart Lane in 44 years as Jay-Jay Okocha dented caretaker manager David Pleat's hopes of securing the Spurs manager's job.
It was Kevin Nolan who scored for Wanderers but Okocha was the inspiration as Spurs, who had kept four clean-sheets in the five previous matches under Pleat, were out-classed.
The Nigerian winger hit the woodwork three times himself and set up a host of chances for others - including the one after 73 minutes which gave Nolan his fourth goal of the season and sent Bolton home with all three points.
Okocha's effort from outside the box was spilled by goalkeeper Kasey Keller and Nolan was on hand to convert the vital goal.
Ironically it was Spurs who began the stronger as Bobby Zamora, Stephen Carr and Robbie Keane all come close - but they were almost the last chances for the home team.
Soon after Okocha set the tone for the afternoon when, out of nothing, he crashed a 20-yard shot against the bar.
Buoyed by that effort, Okocha curled a free-kick just over and then had another shot saved by Kasey Keller.
It was becoming a one-man show as, soon after, the Nigerian dribbled past three defenders before seeing his shot blocked and then rifled another drive over the bar.
Okocha's team-mates - who had won once in their last 10 games - found themselves awakened by his efforts and in the 34th minute Per Frandsen had a shot tipped past the post by Keller.
Tottenham's American goalkeeper, who had not conceded in 330 minutes of football before this game, also had to save from Stelios Giannakopoulos before the break.
The second half started slowly for both teams but by the 73rd minute Bolton finally got the goal their efforts deserved.
At half-time Pleat sent on Helder Postiga for midfielder Gus Poyet to form a three-pronged strikeforce with Keane and Zamora.
But it was Bolton who continued to look likeliest to score and Spurs were saved by the woodwork again after 57 minutes as Okocha's free-kick deflected off team-mate Frandsen on to the bar.
Kevin Davies saw a header tipped over by Keller before Wanderers finally grabbed that goal they so richly deserved.
There was still time for Okocha to hit the woodwork again - a hat-trick of shots against the bar - and had he made it 2-0 Spurs and Pleat could have had no complaints at all.