Stewart Downing's 30-yard strike earned Middlesbrough a draw at White Hart Lane after a Jonathan Grounds own goal had given Spurs the lead.
Spurs dominated the first half and went ahead when Grounds diverted Aaron Lennon's volley beyond Mark Schwarzer.
The home side should have scored more, with Dimitar Berbatov and Jermaine Jenas squandering a number of chances.
Boro equalised when Downing's long-range effort deflected off Jenas's head and into the top corner.
Only Manchester United and Arsenal have scored more goals than Spurs in the Premier League this season, but no other team has let an advantage slip more frequently than the Londoners.
And it was Spurs' lack of killer instinct which again cost them dearly against Middlesbrough.
The home side played with verve and panache in the first half; Berbatov illuminating White Hart Lane with his deft touches and creative brilliance.
But the Bulgarian faltered after the break, and so did his team-mates, as they allowed the visitors back into the game - and nearly let Boro take the three points back to the north east.
In a ping-pong style first half both teams were intent on attacking, with Spurs creating the better chances.
Afonso Alves thought he had put Boro ahead after just two minutes but the Brazilian's tap-in was deemed offside, and from then on it was all Spurs.
Berbatov headed straight at Schwarzer from close range in the 13th minute, while the Boro keeper needed to be quick off his line to stop Jenas seven minutes later after a sparkling run from the midfielder.
The Australia goalkeeper was helpless to prevent the home side taking a deserved lead, however, when Grounds, making his first appearance for six weeks, diverted Lennon's shot into his own goal in the 27th minute.
Berbatov, with his back to goal, delightfully found the diminutive winger at the far post and Lennon's volley made its way into the net via the 20-year-old defender's knee.
Tottenham were not as fluid after the break, and Boro came close to equalising in the 47th minute only for the ubiquitous Lennon to clear David Wheater's goal-bound header off the line.
The home side momentarily worked their way back into the game, with Berbatov again at the heart of the action. The striker should have doubled Tottenham's lead but his six-yard effort was unintentionally deflected onto the post by Emanuel Pogatetz's arm.
As has often been the case this season, though, Spurs were left to rue their profligacy when Downing scored his eighth goal of the season.
The Middlesbrough midfielder cut inside, tried his luck from 30 yards and struck gold when, with the help of Jenas, he beat a statuesque Radek Cerny.
With 15 minutes remaining, Juande Ramos replaced Lennon with Darren Bent as Spurs opted for a 4-3-3 formation in the hope of stopping Boro's increasing dominance.
But Spurs created little, and indeed Alves came within inches from securing the three points for the visitors when his shot whisked past the far post.
• Tottenham head coach Juande Ramos: "We always want to produce the best performance possible but you have to understand the situation the team is in.
"We are in the middle of the table, the points aren't excessively important - we can't reach the top part of the table and we don't seem to be in danger.
"It is not easy to get the maximum motivation when the team is in this situation."