Manchester City were denied by the woodwork five times as a lethargic Bolton grabbed an undeserved win thanks to Gary Speed's late penalty.
In the first half, Antoine Sibierski saw two headers crash off the bar as City played to his aerial strength.
After the break, a Joey Barton drive cannoned back off the post, Kiki Musampa's volley found the bar and Sun Jihai also hit the bar with a drive.
But Bolton snatched the points after Richard Dunne handled in the area.
A combination of Bolton's good fortune and some excellent goalkeeping from Jussi Jaaskelainen had kept them in the game.
Jaaskelainen produced a breathtaking stop to prevent City substitute Stephen Ireland scoring with a fizzing close-range shot.
But the drama came at the very end of the match when Dunne handled and Speed stepped up to coolly convert from the spot to end City's unbeaten run.
The visitors had employed their familiar 4-5-1 formation in order to try and stifle the game.
But City adopted a Bolton-esque way of overcoming the defensive midfield wall - lobbing the ball over the top to make use of Antoine Sibierski's height.
The Frenchman proved highly adept in the air - and especially good at a version of the crossbar challenge.
He was unlucky to see one powerful header smack against the bar and bounce on the top of it on the way down.
And a combination of Jaaskelainen's fingertips and the crossbar prevented him shortly after when he steered Danny Mills' cross goalwards.
He was a little less accurate with his boot, but no less acrobatic, when he jumped to volley Darius Vassell's cross just past the upright.
Musampa had already completed a hat-trick of missed chances by then, twice shooting off target when well-placed and barely testing Jaaskelainen with the other strike.
City had adapted well to the loss of Trevor Sinclair who fell awkwardly on 25 minutes and was unable to continue.
But they could have gone in at the interval paying the price for some slack defending.
Bolton's best chances of the half fell to their two Kevins, Nolan and Davies, but neither men could head the opening goal despite being unmarked.
After the break, City increased the tempo and soon created a chance for Joey Barton, who had not long picked himself up from a nasty challenge by Davies.
But just as the woodwork had denied City twice before, so it did again as Barton's superb left-foot shot thumped the base of the upright.
And the frame of the goal soon frustrated City once more when Musampa's sweet strike struck the crossbar minutes later.
Before that Claudio Reyna had slid in to connect with Vassell's centre, but Jaaskelainen's trailing leg diverted the ball around the post.
By now Bolton were desperately clinging on and had brought on Hidetoshi Nakata for his Premiership debut.
The Japan international blazed over with a rare Bolton effort on goal.
But there was still time for City to hit the woodwork for an incredible fifth time when Jihai unleashed a fierce, angled shot from the edge of the box.
Manchester City boss Stuart Pearce:
"We probably deserved to win the game, let alone draw it. We hit the woodwork five times.
"We gave a penalty away at the end - but Richard Dunne owes me nothing, he has been incredible for me.
"The result, and the manner of it, will galvanise my team and down the line someone will pay for it."
Bolton manager Sam Allardyce:
"We're delighted we've won but we know we're very fortunate. The woodwork saved us on a few occasions, and some great defending and goalkeeping.
"It reminds me of playing Everton earlier in the season. We got mugged there and we've mugged Man City today.
"We caught them napping at the end because we're fit and determined enough to keep going right to the end. We've not played well but we've got a result."
Man City: James, Mills, Dunne, Distin, Thatcher, Sinclair (Jihai 26), Barton (Ireland 81), Reyna, Musampa, Sibierski, Vassell.
Subs Not Used: Fowler, Onuoha, De Vlieger.
Bolton: Jaaskelainen, Ben Haim, N'Gotty, Jaidi, Pedersen, Diouf (Nakata 56), Speed, Faye (Campo 45), Nolan, Giannakopoulos (Gardner 66), Davies.
Subs Not Used: Walker, Borgetti.
Goals: Speed 90 pen.
Ref: M Dean (Wirral).