Jermain Defoe and substitute Frederic Kanoute ensured Spurs got back on the winning trail in a game marred by controversy, following the dismissal of Middlesbrough defender Franck Queudrue in the first half.
Jol was quick to make changes to his side and handed an immediate recall to Rohan Ricketts who has only just returned from a month's loan at Coventry.
Young winger Reto Ziegler was also brought back into the starting line-up with Pedro Mendes partnering Michael Carrick at the heart of the Spurs midfield.
Middlesbrough boss Steve McClaren made no surprise in bringing his heavyweight pairing of Jimmy Floyd Hasselbaink and Mark Viduka back into the attack after they were left out of their midweek UEFA Cup tie.
And it was the away side almost came close to breaking the deadlock on 14 minutes when Stewart Downing's cross found Hasselbaink inside the box.
The Dutch striker cleverly nodded the ball into the path of Ray Parlour who drilled a low shot just past the post.
But Tottenham fought their way back into the game and almost opened the scoring themselves on 18 minutes.
Defoe's free-kick went straight against the Boro wall, but the ball came back to the England striker and he fired a blistering shot which fell inches wide of goal.
And just 60 seconds later, Carrick made space for himself on the edge of the box and struck a 25-yard shot which produced a fine save from Mark Schwarzer.
Defoe came even closer to getting his name on the scoresheet on 35 minutes when Ziegler played him through on the goal.
The prolific forward raced into the box, but fired his effort just over the bar.
The game descended into controversy on 40 minutes when Queudrue made a two-footed challenge on Noe Pamarot and was immediately shown the red card for his actions.
Queudrue refused to leave the pitch, but referee Phil Dowd refused to change his mind and George Boateng was also booked for remonstrating over the decision.
And Tottenham made the extra man count on 48 minutes when Defoe finally got his just rewards when he opened the scoring.
Mendes played the perfect ball into the path of the young star and Defoe made no mistake this time planting a sweet right-foot shot past Schwarzer into the corner of the net for his tenth goal of the season.
Defoe continued to cause all kinds of problems for the Middlesbrough defence and could have got his second of the game on 64 minutes, but this time fired his close-range effort just over the crossbar.
But the home side sealed all three points in bizarre circumstances on 76 minutes after Schwarzer failed to deal with Parlour's backpass.
The Australian keeper kicked the ball straight into the path of substitute Kanoute and the ball rebounded into the back of the net.