He started with a strikeforce of Darren Bent and Jermain Defoe in his first Premier League game in charge of Spurs.
Middlesbrough suffered a pre-match blow when central defender Jonathan Woodgate was ruled out with a leg injury.
Former Portsmouth midfielder Gary O'Neil captained Boro for the first time with regular skipper George Boateng relegated to the substitute's bench.
Boro, who were in desperate need of a win after a poor run of results, showed more self-belief in the early stages than in their previous home game against Chelsea.
They could have taken an early lead when O'Neil hit the ball across the goalmouth to the far post where Stewart Downing just failed to get a foot to it.
It was a glorious chance and Middlesbrough paid the price when the visitors went ahead in the 35th minute.
Bent had the satisfaction of scoring his second Premier League goal with a shot from the edge of the penalty area that went just inside the near post.
Goalkeeper Mark Schwarzer should have made a better attempt at preventing Boro going a goal behind for the tenth time this season.
The goal boosted the visitors' confidence and Boro were struggling to get back into the game especially with their current attacking limitations.
Spurs almost added to their lead before half-time when Defoe shot inches past the far post with Bent just unable to connect with the ball.
There was booing from a section of Middlesbrough fans as the referee blew the half-time whistle.
The Teessiders had a mountain to climb, particularly with an impotent strikeforce, but Jeremie Aliadiere was unlucky not to equalise with a header that brought a brilliant full-length save from Paul Robinson.
Middlesbrough did eventually draw level in the 52nd minute with a stunning 25-yard shot from Luke Young that left England international goalkeeper Robinson helpless.
The goal lifted the crowd and the scorer was mobbed by his delighted team-mates once they could catch him.
Both teams went flat out for a winner in an exciting finale. Overall, a draw was a fair result in a sporting game in which there was only one booking.