A double from Darren Bent looked like it had saved the day, but set pieces proved costly and it was Bolton who took the points via a 3-2 win at the Reebok Stadium on Saturday.
On as a second half substitute, Bent's two goals levelled matters after the home side claimed a two-goal lead and it was the team in black that looked the likely winners until Kevin Davies scored the second of his two goals to snatch victory.
Harry Redknapp made just one change with Wilson Palacios making his debut in place of Jermain Defoe with Luka Modric employed just behind lone striker Roman Pavlyuchenko.
David Bentley set a lively tone for the afternoon when he fizzed in a shot that bounced up in front of Jussi Jaaskelainen, with the goalkeeper just managing to shovel around the post for a corner.
Modric again looked like he was going to be a key element of the afternoon's entertainment, buzzing around and involving himself in the thick of the early action as he conducted his dual role of midfield industry along with skilful support of Pavlyuchenko.
Bolton were not quick to show their hand, but what they did form was a tall, powerful barrier across the pitch. It was the combination of Matt Taylor and Davies and the anticipated threat from set pieces that caused the first alarm, when Taylor centred and the powerful striker thrust his header narrowly over the bar.
A similar set piece from Bentley at the other end was met by the glancing head of Pavlyuchenko at the near post, he didn't quite get enough on it, but one of the players in front of goal should really have gambled and slid in on the passing ball.
The debut-making Palacios was a bundle of energy in midfield alongside Didier Zokora, possibly an ideal combination for a fixture of this nature and they were certainly applying the squeeze in the central area in the opening 15 minutes or so.
Jaaskelainen was forced into an emergency stop 25 minutes in when the scurrying of Aaron Lennon presented Bentley with a chance to smash goalwards. He duly did but the Finn was in position to foil ably.
Carlo Cudicini was tested at the other end when Taylor drilled in from 20 yards and the Italian gathered with considerable confidence.
It was a set piece that engineered our undoing in the 31st minute, an inswinging ball into the danger zone from Mark Davies had three white shirts in a row lining to apply the nod. Sebastian Puygrenier planted his head on the ball and the net was quickly shaking.
Pavlyuchenko, fighting something of a lone battle up top, fired towards goal on the turn a few minutes before half-time but was unable to really work Jaaskelainen.
The shape of the team was altered during the break, Jermaine Jenas making his return to the side, as well as Bent - Zokora and Modric making way. There was a renewed tempo to the approach of the side and Jenas and Bent were quickly to the fore.
Lennon was also posing more of a threat having switched to his natural territory on the right hand side, but testing Jaaskelainen was proving troublesome as moves were breaking down in the final third.
Bolton had no such problems in the 64th minute with a smash and grab raid. Jloyd Samuel swung the ball back to the edge of the area following a clearance, there was a flick-on and Kevin Davies was waiting to fire past Cudicini to double the advantage.
Pascal Chimbonda was added to the mix for his second coming in place of Vedran Corluka and he played a big part in the deficit being reduced with 17 minutes remaining on the clock. Lennon supplied the overlapping full-back and, with a precise low cross, Chimbonda picked out Bent, who managed to steer past Jaaskelainen and into the net.
Just two minutes later a cleared cross from Chimbonda fell at the feet of Palacios and Jaaskelainen saved but could not hold on - cue Bent for his second of the game and a joyous jig towards the travelling Spurs fans.
The team kept knocking at the Bolton back gate, but we paid the price from another set piece on 87 minutes when a Davies came out of a melee strongest from a Taylor corner and somehow squeezed in his header at the near post.
After such a stirring comeback it was a cruel ending.