Bolton recorded a Premiership double over Tottenham with goals in each half from Ivan Campo and Henrik Pedersen. The Spaniard scored after seven minutes, firing in a long-range effort from 25-yards having latched on to a cross from Jay-Jay Okocha.
Okocha, Kevin Nolan and Kevin Davies all went close before the hosts deservedly doubled their advantage when Pedersen converted from close range.
The defeat leaves Tottenham six points clear of the relegation places.
For Wanderers, free of the pressures of a seemingly perennial relegation battle, there is the promise of a best-ever Premiership season and they played some free-flowing football.
Such fare is supposed to be the staple diet of meaningless end-of-season matches, but there was none of the fun of the fair for Tottenham, who have never won at the Reebok.
They never threatened to break that hoodoo and this loss will have done little to lift the pervading mood of doom and gloom at White Hart Lane.
Bolton boss Sam Allardyce recalled Okocha, a decision that paid dividends.
The mercurial Nigerian was on song throughout and set up Campo who saw his effort squirm past Kasey Keller, having taken a wicked bounce off the patchy pitch.
A goal up after seven minutes, the only surprise was that Bolton had to wait so long before scoring a second.
That was in large part due to Keller. The American kept the arrears to one when he clawed away a deflected Nolan shot minutes later and denied Okocha and Davies before the break.
Tottenham's response was toothless and efforts from Jermain Defoe and Simon Davies lacked the bite to trouble Jassi Jaaskelainen, making his 200th Bolton start in goal.
Robbie Keane came off the bench on the hour to add weight to Tottenham's attack, but it was the defence that needed plugging.
Okocha went close to a first Premiership goal of the season with a free-kick before Pedersen finally made it two.
The Dane latched on to a Youri Djorkaeff throughball before twisting and turning Anthony Gardner to a standstill and poking his effort beyond Keller for his third goal in successive games.
David Pleat's side held on to return south with no more damage in defeat and, after a frustrating season, the Tottenham faithful will be hoping for something to celebrate in next weekend's north London derby.
But without a win in six matches and with champions-elect Arsenal flying high, it could be that there will be even less to cheer as Tottenham's season, and Pleat's reign, fizzle out for good.
