A late winner from substitute Glenn Whelan gave Stoke City an unlikely 1-0 victory over a dominant Spurs on a frustrating day at White Hart Lane.
In a game that marked a year in charge for our manager Harry Redknapp, injuries to both Jonathan Woodgate and Aaron Lennon compounded the disappointment in only our third home defeat of his reign.
Woodgate was making his first appearance of the season after returning from the groin injury that has kept him on the sidelines since May.
But he lasted for only 15 minutes of his return after failing to fully recover from an early clash with James Beattie.
However, we were still the better side throughout until Lennon limped off 10 minutes from time, leaving us a man down with three substitutes already used.
The unlikely winner then came as a bitter blow on a day to forget at The Lane.
Woodgate started alongside Sebastien Bassong in the centre of defence with Ledley King not quite fit enough to feature in this fixture.
There were two further changes to the side that defeated Portsmouth last weekend. Jermaine Jenas dropped to the bench in place of Wilson Palacios, who returned from international duty too late to start at Fratton Park.
And Peter Crouch came in for his third league start of the season in place of the suspended Jermain Defoe, sent off against his former club.
Stoke, meanwhile, suffered a blow in the warm-up when goalkeeper Thomas Sorensen pulled out through injury and had to be replaced by Steve Simonsen between the sticks.
The atmosphere inside the ground was teed up prior to kick off by a stirring video shown on the stadium's big screens celebrating the life of the legendary Bill Nicholson, five years on from his passing. It was applauded throughout by our fans.
But it was the visitors who would have had something to be proud of after just three minutes had it not been for some first class defending by the unfortunate Woodgate.
No time for rustiness as Beattie went in to meet a deflected Matthew Etherington cross with Heurelho Gomes stranded, only for the long-haired, banded head of Woodgate to meet the ball in brave fashion and clear to safety.
However, the nasty-looking blow he received to the face in the process meant the defender's comeback was short-lived, and after soldiering on for another 10 minutes, he was replaced by Michael Dawson at the back.
After the early scare, we began to take control and created our first opening on 11 minutes, playing Stoke at their own game with some high balls into their box. And why not, with Crouch proving such a valuable aerial outlet? It was his head that forced Simonsen into a full stretch save after Benoit Assou-Ekotto's deep cross.
On 23 minutes we took a more familiar route towards goal when Lennon picked up the ball in midfield, raced across pitch playing an exchange with Niko Kranjcar on the way, and curled a terrific effort towards the top corner which Simonesen again did well to palm away at full stretch.
Moments later, Bassong should have done better with a volley he put wide at the back post six yards out after Stoke failed to clear their lines from the resulting corner.
But on 26 minutes, there was little more Crouch could have done from the same area, rising to meet Lennon's cross and looping his header over Simonsen, only to see Beattie acrobatically clear off the line.
We were again unlucky just moments later when Kranjcar's low 20-yard drive crashed against the foot of the post.
It was all Spurs at this point, but Stoke did tighten up towards the end of the half and the teams remained on level terms at the break.
However it was still backs to the wall for the visitors into the second half. It took some desperate defending from both Ryan Shawcross and Dean Whitehead to deny Crouch on 48 minutes when a Robbie Keane shot was parried out to him with the goal gaping.
More desperation from the visitors on the hour mark when Crouch climbed to meet Lennon's cross, again Simonsen kept it out, and Whitehead did just enough to put Vedran Corluka off his shot six yards out.
We clearly needed something a little extra, so Redknapp then threw on Roman Pavlyuchenko in place of Keane, meaning two big men up front.
Jenas was also introduced with 20 minutes remaining in place of Tom Huddlestone to add a little more forward drive from midfield.
But much of that was stolen from us 12 minutes from time when Lennon went down under a challenge from Whelan, who had been introduced in place of Rory Delap just before the hour mark, and could not continue.
With the scores still at 0-0 and with a man advantage, the unlikely scenario of Stoke coming away with all three points was made apparent when Tuncay worked an opening and shot wide in what must have been the Potters' first attack since the third minute.
Five minutes from time, however, came the shocking reality.
Ricardo Fuller chased down a lost cause into our bottom left-hand corner, got the better of Assou-Ekotto and pulled back for Whelan to smash home from 12 yards.
It was a bitter blow and hardly deserved, but that is the harsh nature of the Barclays Premier League summed up in one fail swoop.
We never recovered. Everton are next up in the Carling Cup on Tuesday night before a hotly-anticipated trip to the Emirates a week away.
Spurs (4-4-2): Gomes; Corluka, Woodgate (Dawson, 15), Bassong, Assou-Ekotto; Lennon, Huddlestone (Jenas, 70), Palacios, Kranjcar; Crouch, Keane (Pavlyuchenko, 62)
Subs not used: Cudicini, Bale, Hutton, Naughton
Stoke (4-4-2): Simonsen; Wilkinson, Faye, Shawcross, Collins; Delap (Whelan, 57), Diao, Whitehead, Etherington; Beattie (Tuncay, 69), Fuller (Higginbotham, 89)
Subs not used: Cort, Lawrence, Pugh, Kitson