Davies heads the crucial late winner that broke Tottenham's hearts
Kevin Davies struck four minutes from time to snatch an unlikely victory for Bolton after Spurs had bravely fought back from two goals down late on.
Bolton controlled the early proceedings and deserved their lead when Sebastien Puygrenier headed in, before Davies fired into the corner to make it 2-0.
Substitute Darren Bent scored twice in two minutes from close-range, though, to put Spurs right back into the game.
But Davies had the final say when his header earned Bolton a thrilling win.
Three points see Bolton leapfrog their fellow strugglers and up into 12th in the table, and also spared boss Gary Megson's blushes after his side had contrived to throw away a two-goal lead for the second time in four days.
Megson relieved to get crucial win
It was cruel luck in the end for Bent, though, who marked his first appearance since his now infamous miss against Portsmouth denied Spurs a home win a fortnight ago with two goals that looked like securing an unlikely point for the visitors.
The brace might yet secure his short-term future at the club, especially with Jermain Defoe absent with a foot injury, but in the end it counted for little thanks to Davies's late strike - a goal which made it six straight away defeats for the Londoners.
Bolton's win - their first in six matches - and the performance was a timely boost for Megson, though, after his barracking from his own fans in Wednesday's 2-2 draw with Blackburn.
Davies was the inspiration and a constant thorn in the side of Spurs' defence, while Ariza Makulula had the best of the early chances when he sliced wide from 18 yards out.
Full debutant Mark Davies also went close for the hosts, looping a header over unmarked from 12 yards, while namesake Kevin headed a Matt Taylor free-kick over with the visitors' apparent aerial frailty exposed all too often.
Spurs' best moments often came through the resurgent David Bentley, who twice tested home keeper Jussi Jaaskelainen with drilled efforts from range, while debutant Wilson Palacios was full of hassle and harry.
Redknapp bemused by defeat
But for large parts of the game Spurs were bereft of inspiration and it was hardly against the run of play when Bolton took the lead and even less surprising it came from a set piece.
Mark Davies was the creator with a free kick, Puygrenier making the most of some hopeless marking in the Spurs box, losing Didier Zokora to head home from six yards for his first goal for Bolton since joining from Zenit St Petersburg.
Spurs boss Harry Redknapp's response at the break was to replace the ineffective Luka Modric and Zokora with Bent and Jermaine Jenas, but despite a wealth of possession, the visitors' continued lack of sparkle ensured the Trotters remained comfortable.
And when Kevin Davies latched on to Gary Cahill's flick to drive across Carlo Cudicini and into the far corner of the Spurs net, the hosts' win looked assured.
Great day for proud Davies
However, the Trotters reckoned without Bent and Chimbonda's intervention.
The former reduced the deficit when he swept in Chimbonda's cut-back from close range and, just two minutes later, levelled it up when he pounced after Jaaskelainen could only parry a snapshot from Palacios.
There was yet another twist in the tail, though, as Davies stooped to head in Matt Taylor's corner, the ball squeezing past Bentley on Tottenham's near post, to seal the victory.
Bolton boss Gary Megson: "When we were pegged back to 2-2, I didn't think the game at that stage was a drawn game, I thought we much better than they were and a lot more positive - they've got some quality players but I felt we deserved our lead.
"Thankfully, though, we've got Matty Taylor's fantastic deliveries and Kevin Davies's heading ability and that's pulled us through.
"As for any transfer activity - the Miguel Veloso deal is not going to happen. We don't want to run a fool's errand, and that looks a bridge too far.
"But we've got two bids in at the moment - one for a Premier League player and one Championship player - and I would expect some business to happen over the next couple of days."
Tottenham manager Harry Redknapp: "That's the last four away games in which we've dominated proceedings and then gifted the opposition - and these are teams that are around us at the bottom end of the table - a winner two or three minutes from time.
"Sitting there with five minutes to go I wouldn't have taken a draw because we were pummelling them and there was only one team who I thought would win it and that was us. But we've thrown it away again.
"As far as transfers go, no-one will be leaving this club in the next few days, I'll tell you that, because we can't afford for anybody to leave. But I definitely think we need one or two more players - strong players - to come in, so if something can be done, we'll do it.
"And as for Darren Bent - he has absolutely nothing to prove to me, I know he's a good player. He was excellent today, has 14 goals for the season, and we need him here - especially with Jermain Defoe out with what looks a nasty injury."
Bolton: Jaaskelainen, Steinsson, Cahill, Puygrenier (Andrew O'Brien 79), Samuel, Taylor, Mark Davies, Muamba, Gardner, Kevin Davies, Makukula (Smolarek 61). Subs Not Used: Al Habsi, Riga, Shittu, Basham, Obadeyi.
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