Bolton substitute Henrik Pedersen grabbed a late winner to maintain his side's impressive start to the season and dent Tottenham's hopes of getting back in the top six.
Tottenham fans turned up in their thousands to pay tribute to former manager Bill Nicholson who sadly passed away on the eve of the game.
But the Spurs players could not make it a day to remember as Bolton showed they are serious contenders at the top of the Premiership.
Head coach Jacques Santini made the bold decision to leave England star Jermain Defoe on the substitutes bench and recall Fredi Kanoute to the starting line-up.
And young winger Johnnie Jackson was also handed a recall to the side after Thimothee Atouba suffered knee ligament damage during the 1-0 defeat against Portsmouth last Monday.
Bolton boss Sam Allardyce opted for an attacking formation with Ivan Campo ruled out through injury.
Kevin Davies partnered El Hadji Diouf and Stelios in a 4-3-3 system with Jay Jay Okocha playing just behind the three forwards.
Tottenham created the first opportunity of the game in the fifth minute when Robbie Keane made space for himself on the edge of the box and fired in a shot which flew just past the post.
But Allardyce's attacking formation paid off straight away when the visitors broke the deadlock in the tenth minute.
Gary Speed whipped a fierce free-kick into the penalty box and Radhi Jaidi reacted the quickest to head the ball past the stranded Paul Robinson in the Spurs goal.
Okocha could have doubled Bolton's lead in the 20th minute when he weaved his magic outside the area as he eluded the challenge of three Tottenham defenders, but failed to get his shot on target.
Tottenham could have got back on level terms four minutes later when Bolton keeper Jussi Jaaskelainen failed to hold on to a high ball into the box.
The rebound fell kindly to Jackson whose thumping drive was superbly beaten out by Jaaskelainen and away to safety.
The home side continued to push for an equaliser and Kanoute's 20-yard shot produced another fine save from Jaaskelainen diving low down to his left.
Santini's side finally got their just rewards when they grabbed an equaliser four minutes before the interval.
Noureddine Naybet played a ball in to Kanoute who produced a sublime piece of skill to release Keane into the penalty box.
The Republic of Ireland international made no mistake, this time striking the ball through the legs of Jaaskelainen and into the back of the net.
Okocha continued to cause problems for the Tottenham defence and in the 48th minute, he broke free once again and struck a blistering 25-yard drive which flew just over the crossbar.
Bolton had a golden chance to add a second goal just after the hour. Davies' high ball over the top of the Tottenham defence fell to Stelios who found himself unmarked at the far post.
But with the goal at his mercy, the Greek international volleyed the ball inches past the post.
Bolton regained their lead in the 73rd minute, but it needed three attempts before the ball finally found the back of the net.
Okocha's shot was well beaten out by Robinson. The rebound fell to Stelios whose close-range shot produced an even better save from the England international.
But the ball once again fell kindly to a Bolton player and Pedersen at the third time of asking slotted the ball into the back of the net.
Tottenham were desperately unlucky not to grab an equaliser with 11 minutes left when Pedro Mendes' cross found Kanoute, but the Mali international saw his header come back off the post.
MAN OF THE MATCH: Jay Jay Okocha (Bolton) - The Nigerian's trickery was a constant threat to Spurs' beleaguered defence.