Stoke City substitute Glenn Whelan snatched a late winner at White Hart Lane to ruin Harry Redknapp's first anniversary as Tottenham Hotspur manager.
With Jermain Defoe suspended for the Barclays Premier League match, Spurs could not unlock a Stoke defence assembled by boss Tony Pulis, who was a player under Redknapp at Bournemouth.
Peter Crouch had two efforts cleared off the line, both by James Beattie, and Niko Kranjcar struck the post - then the visitors stung them at the end in spectacular fashion when Whelan found the top corner.
It was this weekend last year that Redknapp arrived from Portsmouth to save Spurs from relegation and in the end they nearly ended up qualifying for Europe.
Spurs have not looked back since and have Champions League ambitions after their promising start to the campaign. A video shown on the big screen marking the fifth anniversary of Bill Nicholson's death, their double-winning manager, shows what they have to live up to.
Stoke did too by frustrating them and hitting them with a sucker punch at the death. They showed why they have top-half aspirations of their own.
acrobatic clearance
An illness to Thomas Sorensen meant he was replaced by Steve Simonsen in goal and Leon Cort was promoted to the substitutes' bench but the disruption did not affect the visitors at all.
Salif Diao's ball over the top gave Matthew Etherington an early sight of goal. Kranjcar blocked the volley but Jonathan Woodgate took a boot to the face when he was needed to clear the danger at the far post.
On his first appearance of the season, it was Woodgate's only meaningful contribution as the knock forced him off before the quarter of an hour mark.
With Fabio Capello watching in the stands, Tom Huddlestone was looking to show his range of passing, while Crouch gave an early example of how dangerous he is in the air.
Kranjcar's ball into the penalty area was hopeful but Crouch leapt above the Stoke defence and forced Simonsen into a finger-tip save as the ball looped towards the far post.
Aaron Lennon forced Simonsen into another save when he checked inside Andy Wilkinson, Robert Huth's replacement due to the centre-back's suspension, and curled an effort that would have found the top corner.
The England winger then provided a chance that required an acrobatic clearance from Beattie. Crouch got on the end of the cross and beat Simonsen with his lobbed header but Beattie hooked clear when most of the crowd thought the opener had been scored.
ten men
Kranjcar then hit the base of the post after latching onto Crouch's flick as Spurs increased the pressure.
Republic of Ireland manager Giovanni Trapattoni also attended the match, with his skipper Robbie Keane forcing a save from Simonsen early in the second half.
Wilson Palacios slid the ball through to the Spurs skipper and Simonsen parried the effort away, with Ryan Shawcross and Wilkinson clearing as Crouch closed in.
Stoke were looking to pounce on the counter-attack and Pulis was jumping across the dug-out when Beattie had sight of goal from Etherington's cross but he could not direct his header.
At the other end, Beattie cleared another Crouch effort off the line and Vedran Corluka could not connect when the rebound fell to him.
The hour of goalless football led to Redknapp replacing Keane with Roman Pavlyuchenko.
Lennon headed down the tunnel after injuring his ankle, although he had to explain more than once to the bench that he could not carry on. Spurs played the rest of the game with 10 men.
The winner came four minutes from full-time when Ricardo Fuller held the ball up in the corner before tricking Benoit Assou-Ekotto and pulling the ball back for Whelan, the 57th-minute replacement for Rory Delap, to lash into the top corner off the post.
Kranjcar thought he should have won a penalty in stoppage-time.
