Henrik Pedersen scored the winner for Bolton on an emotional day at Spurs following the death of their legendary former manager Bill Nicholson.
Bolton took a deserved early lead when Paul Robinson flapped at Gary Speed's free-kick and Rahdi Jaidi headed home.
Spurs looked lethargic and offered little until just before the break, a passing move of rare quality ending with Robbie Keane firing the ball in.
But Pedersen came off the bench to tap in a rebound to steal all three points.
The passing of Nicholson clearly had an effect on the White Hart Lane crowd, with the atmosphere muted from kick off.
If the script was written for Spurs to round off an emotional day with a victory, Bolton had not read it and with the first chance they went ahead.
Speed's free-kick from the right landed on Jaidi's head six yards out and he directed it into the corner of the net, with Robinson left flapping behind the Tunisian.
Spurs were really struggling to find any sort of form and their passing was woefully off-target as Bolton dominated the game in the centre of the midfield, with Speed and Jay-Jay Okocha combining well.
As the half wore on the hosts slowly improved, with Freddie Kanoute's left-foot strike from 20 yards that Jussi Jaaskelainen gathered appearing to galvanise both the players and the crowd.
Four minutes before the break they found an equaliser, and it was a goal the great Spurs team of the 1960s would have been proud of.
Spurs' Robbie Keane (centre) tussles with two Bolton players
Jamie Redknapp passed to Pedro Mendes and he fed Kanoute on the edge of the box, the Mali striker beautifully flicking the ball into the path of Keane to rifle the ball in between Jaaskelainen's legs and into the net.
Having finished the first half strongly Spurs were soon on the back foot again after the break, Okocha going close with two long-range shots and Stelios lashing across the face of goal.
But once again Jacques Santini's side moved up a gear, and Keane's weaving run was cynically ended on the edge of the Bolton box by Jaidi, Redknapp wasting the resulting set-piece.
Santini sent on Jermain Defoe to increase Spurs' attacking potential but Sam Allardyce replied by immediately taking off Kevin Nolan and bringing on Pedersen.
It was the visitors who profited, as Okocha and Stelios saw shots saved by Robinson and an unmarked Pedersen slotted in from six yards.
Spurs replied with Defoe blasting a shot wide and soon after Mendes crossed for Kanoute to head against the post.
But on a day when Spurs paid their respects to the man who made them such a force in the English game, the present side could not muster an equaliser to send the supporters home happy.
Tottenham: Robinson, Pamarot, Naybet, King, Gardner,
Davies (Ziegler 80), Pedro Mendes, Redknapp (Davis 78),
Jackson (Defoe 70), Kanoute, Keane.
Subs Not Used: Keller, Brown.
Goals: Keane 41.
Bolton: Jaaskelainen, Hunt, Jaidi, N'Gotty, Gardner,
Diouf (Hierro 81), Speed, Okocha, Nolan (Pedersen 72),
Subs Not Used: Poole, Ferdinand, Fadiga.
Goals: Jaidi 11, Pedersen 75.
Ref: C Foy (Merseyside).