Wanderers were cruelly denied a share of the spoils as Niko Kranjcar came off the bench to decide an action-packed encounter at White Hart Lane.Harry Redknapp's side had taken an early lead in dramatic circumstances after Rafael Van der Vaart had converted from the penalty spot after just five minutes.
The Croatian midfielder drilled in a stoppage time winner after Bolton had earlier fought back to level through Daniel Sturridge's second goal in as many games since joining from Chelsea.
Van der Vaart missed another spot-kick just 60 seconds after his opener but, unfortunately, when Wanderers themselves felt they should have been awarded a chance to take the lead in the second-half from 12 yards, referee Mark Clattenberg turned away appeals after Gary Cahill had taken a tumble under a challenge from Steven Pienaar inside the area.
After his exploits against Wolves on his debut three days prior, Owen Coyle handed Daniel Sturridge his first start for the Whites in what was an extremely attack-minded first eleven. Johan Elmander was shifted over to the right side of midfield as the on-loan Chelsea front man partnered Kevin Davies in attack.
Harry Redknapp had Michael Dawson back available for selection after his enforced one-match suspension for a straight red card against Fulham in the FA Cup, and the former Nottingham Forest defender slotted back in at centre-half alongside William Gallas.
Wanderers, playing in their blue away strip, almost got off to the perfect start with just three minutes played when the front two of Sturridge and Davies combined to carve out an opportunity for Elmander. The Swede made the most of some hesitant defending by the hosts and if it had not been for some alert goalkeeping by Gomes, Bolton would have been 1-0 up.
But as it was, a five-minute period of unbelievable football action followed as Spurs went straight up the other end of the pitch to get themselves an early advantage.
Firstly, Kevin Davies was adjudged to have handled a Rafael Van der Vaart effort inside his own six-yard box by referee Mark Clattenburg, who had no hesitation in awarding a spot-kick for Tottenham.
Van der Vaart stepped up to put the ball in the corner of the net past Jaaskelainen's valiant dive - but just two minutes later the Dutchman had another opportunity from 12 yards to double his team's advantage.
Sensationally, in Spurs' first attack after the restart, Clattenburg was once again involved the thick of the action as he pointed to the spot for a second time when Aaron Lennon took a tumble under a Sam Ricketts challenge.
The home fans were delirious when Van der Vaart again placed the ball into the back of the net but those celebrations were cut short when a retake was ordered for encroachment. And in spectacular fashion, the former Real Madrid man put his second attempt wide of the post, much to Wanderers relief.
Understandably, Bolton were rattled by the early set-backs, but after surviving another scare when Peter Crouch forced Jaaskelainen into action after collecting a cross-field pass from Vedran Corluka, Owen Coyle's men began to reassert themselves on the contest.
Elmander towered to head a Matt Taylor centre against the crossbar on 20 minutes and after making a well-timed sprint down the right channel minutes later, Sturridge turned inside Dawson before firing an effort into the side-netting of Gomes' goal.
The pace refused to relent as the game ebbed and flowed. In quick succession, Jermain Defoe had a goal ruled out for offside, Paul Robinson made a goal-saving challenge on Peter Crouch and Wilson Palacios carried the ball through the midfield before bringing a fine save out of Jaaskelainen.
Just like the first-half had started, it ended in controversial fashion as Mark Clattenburg awarded Tottenham their third penalty kick of the afternoon for an apparent handball against Ricketts. But after consultation with his assistant, the official over-ruled his decision after Crouch had been judged to have ventured into an offside position in the build-up.
Tottenham were dealt a blow at the start of the second-half when Rafael van der Vaart failed to reappear - presumably through injury - with Steven Pienaar his replacement. As for Bolton, Owen Coyle sent out the same set of players that given their all in the opening 45 minutes.
The home side started the period brightly as they pressed and probed in midfield areas, however after taking ten minutes to settle into the half, Wanderers found themselves back on level terms after Sturridge capped-off a swift counter-attack with a wonderfully taken equaliser.
The goal stemmed from great build-up play in midfield from Mark Davies, who carried the ball all of 20 yards before releasing the 21-year-old striker. And with a first-time left foot effort, Sturridge drilled under Gomes from the edge of the area to make the score 1-1.
It could, and perhaps should, have got even better for Bolton just before the hour mark when they were denied a clear-cut penalty when Cahill was sent crashing to the turf inside the box under a late tackle from Pienaar. The Wanderers bench were fuming at referee Clattenburg's judgement and, to add to the frustration, the central defender was booked for simulation.
As expected, Tottenham offered a response after parity was restored and Wanderers had to dig deep to keep the scores level. Within the space of 60 seconds Jemain Jenas sent a 25-yard free-kick crashing against the outside of the post and Jaaskelainen produced the save of the game when he raced from his line to block a Pienaar effort from inside the six-yard box.
With just over 20 minutes remaining, Chung-Yong Lee was thrown into the fray in place of the hardworking Elmander, and within 60 seconds of his introduction the South Korean had been pole-axed in a rash tackle from Jenas. The England international was extremely lucky to escape with just a booking after his knee-high lunge.
The winger's presence certainly had a desired effect as Wanderers, buoyed by their earlier equaliser, sensed all the points were there for the taking. Holden drilled wide from outside the area and Sturridge - from a similar position to which he had scored - had another attempt well blocked by Dawson.
The game became more and more stretched as it entered the final stages as further attacking substitutions were made by both managers. Indeed, the normally defence-minded Fabrice Muamba made a couple of surging runs from central midfield as Wanderers pressed for a late winner.
But cruelly, it was Tottenham who grabbed the decisive goal in stoppage time. Niko Kranjcar - another substitute - unleashed a left foot thunderbolt from outside the box which hit the back of the net despite Jaaskelainen's best efforts, leaving Bolton pointless when they could have easily recorded all three.
Spurs: Gomes, Lennon, Jenas, Van der Vaart (Pienaar 46), Palacios (Kranjcar 77), Gallas, Crouch (Pavlyuchenko 73), Defoe, Dawson, Corluka, Assou-Ekotto, (Subs: not used: Cudicini, Hutton, Bassong, Sandro)
Wanderers: Jaaskelainen, Ricketts, Knight, Cahill, Robinson, Elmander (Chung-Yong 67), Mark Davies, Holden (Muamba 86), Taylor (Petrov 76), Sturridge, Kevin Davies (Subs not used: Bogdan, Klasnic, Rodrigo, Wheater)