Carlos Tevez scored with the last kick of the game to earn Manchester United a draw at Spurs, but they slip behind Arsenal to second in the league.
Tevez left it very late to earn United a point away at Tottenham
Tevez latched on to a corner from substitute Nani and volleyed into the net to break Spurs' hearts after a magnificent display from the home side.
Dimitar Berbatov put Spurs ahead from close range after Aaron Lennon's cross was parried away by Edwin van der Sar.
Robbie Keane missed a clear-cut chance and was made to pay when Tevez struck.
The late goal was desperately harsh on Tottenham, who had produced a defensive display the like of which White Hart Lane regulars will not have seen for years.
Michael Dawson and debutant Alan Hutton in particular were imperious and United rarely looked like getting anything out of the game.
Their late show rescued a point, but the draw means they slip to second in the Premier League after Arsenal's 3-1 victory at Manchester City earlier in the day.
In a week that will see United honour the vicitms of the Munich air disaster 50 years ago, the visitors struggled in a laboured, disjointed display.
Spurs were in the ascendancy from the start and after Owen Hargreaves turned a dangerous Berbatov cross over his own crossbar, from their next attack the hosts went in front.
Jermaine Jenas surged down the right and when his run was halted by Hargreaves, Lennon took over, crossed from the byeline and after Van der Sar parried it out, Berbatov had the simple task of tapping in.
United were furious, claiming that Jenas handled the ball into Lennon's path, but having fallen over backwards it would have been harsh to have penalised him.
Spurs ploughed forward again and Lennon's trickery earned him space to cross down the right, Berbatov uncharacteristically volleying high into the stand from 15 yards.
United were struggling and an unhappy Sir Alex Ferguson sent his team out early for the second half and replaced Hargreaves with former Spurs midfielder Michael Carrick.
But they should soon have been 2-0 down, Berbatov brilliantly skipping past three players and teeing up Keane, the striker shooting straight at Van der Sar from 18 yards when he had time and space to take the ball on.
Ferguson made a double change on the hour, Anderson and Nani brought on in place of Ryan Giggs and Paul Scholes, but still Spurs kept control of the midfield, with the revitalised Jenas again outstanding.
Nani did manage to leave his mark on Pascal Chimbonda, the Portuguese booked for a shocking lunge on the full-back.
Rooney was then cautioned for diving - a booking that will rule him out of next Sunday's Manchester derby - before United threw everything forward in search of an equaliser.
Tevez had been anonymous, but the Argentine left it until the last possible moment to earn some space from a corner and direct the ball past Radek Cerny to leave the home fans heartbroken.
Tottenham assistant manager Gus Poyet:
"We are disappointed they scored so late but we knew we needed to score that second goal to kill it off.
"When you don't score the second it is hard to defend and unless you do it for 90 minutes, you will get punished.
"But we work, we have understanding, confidence and they are all learning. We are slowly becoming a good team."
Manchester United boss Sir Alex Ferguson:
"We had seven booked but my problem is with the referee.
"Ronaldo is hacked down, but Jermaine Jenas gets nothing. Then Wayne Rooney is booked for diving, Tom Huddlestone dives and is not booked. It's chaos.
"I must say, Spurs were very good and must take credit. They are on the up, Juande Ramos has done a fantastic job."
Tottenham: Cerny, Chimbonda, Dawson, Woodgate, Hutton, Lennon (Boateng 79), Jenas, Huddlestone, Malbranque, Berbatov, Keane (O'Hara 90).
Subs Not Used: Robinson, Lee, Taarabt.
Booked: Woodgate, Huddlestone, Cerny.
Goals: Berbatov 21.
Man Utd: Van der Sar, Brown, Ferdinand, Vidic, Evra, Ronaldo, Hargreaves (Carrick 46), Scholes (Anderson 60), Giggs (Nani 60), Rooney, Tevez.
Subs Not Used: Kuszczak, O'Shea.
Booked: Van der Sar, Ronaldo, Brown, Nani, Vidic, Rooney, Tevez.
Goals: Tevez 90.
Ref: Mark Clattenburg (Tyne & Wear).
BBC Sport Player Rater man of the match: Tottenham's Alan Hutton on 7.86 (on 90 minutes).
Please note that you can still give the players marks out of 10 on BBC Sport's Player Rater after the match has finished.