Robbie Keane's late strike helped Spurs to all three points at the expense of Middlesbrough in a match that saw both teams finish with 10 men.
Keane celebrated his goal in typical fashion
Spurs took the lead thanks to a fine volley from Bulgarian Dimitar Berbatov early in the second half.
Robert Huth equalised for Boro with a fierce strike inside the area, before substitute Keane smashed in a superb shot from 25 yards out.
Didier Zokora and George Boateng saw red after a mass brawl late on.
The incident provided a bitter end to what was an entertaining and, largely, tame affair.
It seemed like it would not be Tottenham's day following a first half that saw the north London side miss a plethora of chances that came their way.
Spurs hot-shot Jermain Defoe twice came close, but his 20-yard free-kick dipped too late and then his stinging shot was palmed away by Mark Schwarzer.
His team-mate and England Under-21 star Huddlestone also went close on a couple of occasions and must have impressed national team coach Steve McClaren, who was in the stands.
The teenager anchored the Spurs midfield superbly, but also had the energy to venture forward and test the Boro goalkeeper, with a 20-yard strike that flew narrowly over followed by a surging run and slightly wayward shot.
Defoe's partner in attack, Berbatov, often frustrates, and he did so in the opening 45 minutes.
But just a minute after the restart, he found his touch, executing a wonderful piece of skill to send the home fans delirious.
Huddlestone dinked in a free-kick from the left edge of the area to Chimbonda on the right who nodded the ball into the path of the Bulgarian striker.
Berbatov swivelled and in a single action placed his volley beyond the reach of Schwarzer.
If it was not for the Boro keeper, the score could have been more handsome for Tottenham.
Defoe was twice denied after the break by the Australia international, who rushed out of his area to block point-blank.
At the other end there were few chances of note.
A Huth free-kick had to be punched away by Paul Robinson, while the follow-up saw James Morrison sweep his shot just wide of the keeper's left-hand upright.
The storm after the calm
Spurs were cruising until they suffered the jitters. The home defence failed to clear Stewart Downing's free-kick from the left and Huth made them pay, thrashing in from six yards.
Boro hardly had time to celebrate, when Keane, who had just been brought on, was fed by Huddlestone's quick free-kick and lashed in a stunning shot.
Game set match, yes, but the drama was not over.
Spurs midfielder Aaron Lennon, lively throughout the match, was a little too lively when he appeared to push over Boateng.
The Dutch player rose to retaliate, but before he could reach Lennon, Zokora rushed in to take matters into his own hands.
Their team-mates soon became involved in an ugly melee before referee Mark Halsey stepped in and brandished red cards to Zokora and Boateng.
Tottenham boss Martin Jol:
"If you waste six or seven chances to score the second goal then it's always going to be difficult.
"A 1-0 lead is never enough. I would have been upset if we had not won."
Boro boss Gareth Southgate:
"There's a challenge between George (Boateng) and one of their players. Then George gets bundled over.
"I don't think he was doing anything other than stopping people running at him. Hopefully, the referee will have another look at the incident."
Tottenham: Robinson, Chimbonda, Dawson, King, Lee, Lennon, Zokora, Huddlestone, Malbranque (Keane 81), Defoe (Tainio 89), Berbatov, Keane (Murphy 90).
Subs Not Used: Cerny, Stalteri.
Sent Off: Zokora (88).
Goals: Berbatov 48, Keane 84.
Middlesbrough: Schwarzer, Xavier, Huth, Woodgate, Pogatetz, Taylor (Arca 46), Cattermole (Viduka 57), Boateng, Downing, Yakubu, Christie (Morrison 46).
Subs Not Used: Jones, Parnaby.
Sent Off: Boateng (87).
Booked: Arca, Huth, Pogatetz.
Goals: Huth 80.
Ref: M Halsey (Lancashire).