Jose Mourinho thought the reigning champions had turned a corner, but Eddie Howe's visitors inflicted an eighth defeat of the season, the fourth at home.
Glenn Murray headed in moments after coming off the substitutes' bench and, while there may have been a hint of offside, the Cherries deserved their win in front of Chelsea owner Roman Abramovich, who could yet wield the managerial axe.
Bournemouth won the Championship last season and Chelsea the Premier League, with the victory showing not just how far the Cherries had come, but how far the Blues have fallen.
Diego Costa started as a substitute for a second straight game, but, unlike at Tottenham, the striker was not left to brood for the entire 90 minutes and came on at half-time.
Costa's presence was limited until he fouled Adam Smith, was denied a penalty when his cutback hit Simon Francis on the arm and then was shown a yellow card for a foul on Matt Ritchie in quick succession.
Pedro, or Costa, should have scored 15 minutes from time, but neither could get on the end of Branislav Ivanovic's dangerous cross as Chelsea became increasingly frustrated by referee Mike Jones' decisions.
And Mourinho will be furious when he sees the replays of Murray's winner, which came when Thibaut Courtois flapped at a corner and the former Crystal Palace striker headed in.
Chelsea face further examinations against Porto and Leicester in the next 10 days, while the Cherries next play Manchester United.
Eden Hazard received a written report after his Tottenham display as Mourinho wanted to leave no doubt over his delight at the performance.
His first-half appraisal, continuing as Chelsea's "false nine", is unlikely to have been glowing.
The Belgian had a chance to end his search for a first goal of the season in his 20th game in the opening moments, but his shot was less than convincing and straight at Artur Boruc, the goalkeeper back from a six-week injury absence.
Hazard would have been marked down by Mourinho soon after, too, when he lost the ball to Smith, in for the ill Sylvain Distin, and Junior Stanislas shot
Fortunately for Hazard, Gary Cahill blocked.
Courtois was back for the first time in three months after his knee injury and soon showed why he was immediately restored, saving well from Stanislas.
Joshua King could not get the rebound away and then fired at Courtois at the near post.
The visitors attacked with pace and the Blues were vulnerable, particularly out wide.
Costa, who flung his substitutes' bib at Mourinho at the end of last Sunday's draw at White Hart Lane, needed help from John Obi Mikel to put on his green bib after 29 minutes before warming up on the touchline.
Chelsea were ponderous in possession and appeared to lack a presence up front, with Boruc saving from Hazard, Pedro and Oscar.
Mourinho had seen enough, sending on Costa for Oscar.
The muted half-time boos turned to applause just at the sight of the Spain striker going on.
Nemanja Matic, wearing a protective mask, should have done better than head over Willian's cross before Jones ignored Costa's penalty appeal before booking the striker.
Costa stretched to toe-poke Cesc Fabregas' ball over the top, but Boruc saved.
Murray scored eight minutes from time and Bournemouth might have had two more when Ritchie and Harry Arter fired wide on the counter-attack in a memorable win.
TWEET OF THE MATCH
"I think it was very considerate of Chelsea to swap sides with Leicester this season." - Gary Lineker (@GaryLineker) sums up change of fortunes for both Chelsea and Leicester as the champions suffer another Premier League defeat.
PLAYER RATINGS
Chelsea
Thibaut Courtois: 6 (out of 10)
Branislav Ivanovic: 6
Baba Rahman: 5
Kurt Zouma: 6
Gary Cahill: 7
Cesc Fabregas: 4
Nemanja Matic: 6
Willian: 6
Eden Hazard: 5
Oscar: 4
Pedro: 6
Substitutes:
Diego Costa (Oscar, HT): 5
Bertrand Traore (Rahman, 83): 5
Loic Remy (Fabregas, 83): 5
Bournemouth
Artur Boruc: 8
Charlie Daniels: 7
Simon Francis: 7
Steve Cook: 6
Adam Smith: 7
Harry Arter: 7
Dan Gosling: 6
Andrew Surman: 7
Matt Ritchie: 8
Junior Stanislas: 7
Joshua King: 7
Substitutes
Glenn Murray (King, 80): 7
STAR PLAYER
Boruc returned from a six-week absence to frustrate Chelsea, saving from Hazard, Oscar, Pedro and Costa.
MOMENT OF THE MATCH
Murray came off the substitutes' bench to score Bournemouth's winner
There was a hint of offside as he nodded in at the post after Chelsea failed to deal with a corner, with Courtois flapping.
VIEW FROM THE BENCH
Mourinho made one change following the Tottenham draw he regarded as Chelsea's best performance of the season
But Costa was out of the starting XI for a second straight game
Chelsea were again ponderous in possession and lacked a presence, which barely changed when Costa came on at half-time
Bournemouth were without Sylvain Distin due to illness, so Smith came in and goalkeeper Boruc was back
The Cherries huddled round Howe and assistant Jason Tindall at any lengthy break in play and enacted the game plan perfectly.
MOAN OF THE MATCH
Fabregas floundering
One ball to Costa aside, the Spain playmaker again struggled to make a meaningful contribution.
WHO'S UP NEXT
Chelsea v Porto (Champions League, Wednesday, December 9)
Bournemouth v Manchester United (Barclays Premier League, Saturday, December 12)
Source : PA
Source: PA