Djibril Cisse's 82nd minute winner means Juande Ramos' men are still looking for their first points of the new season after a 2-1 defeat at the hands of Sunderland at The Lane.
An evenly-matched and an at times exciting encounter could have gone either way, but the former Liverpool striker came off the bench to grab victory after we had come back from a goal down.
Kieran Richardson had given Roy Keane's side the lead 10 minutes after half-time, but we worked hard to get ourselves back into the game and were rewarded by Jermaine Jenas' 72nd minute equaliser.
But it wasn't to be, and we go into next weekend's London derby with Chelsea at Stamford Bridge desperate to kick-start our 2008/09 campaign.
Spurs had the better of the early exchanges with much of their threat coming from wide areas during the first half.
Didier Zokora and Aaron Lennon on the right, with Gareth Bale and Benoit Assou-Ekotto on the left kept a constant flow of good delivery coming into Sunderland's box.
Add to that the threat of David Bentley from set-pieces, and big Black Cats centre-halves Nyron Nosworthy and Danny Collins had their work cut out for them.
Nosworthy in particular had to be at his best on 18 minutes when turning a hanging Lennon cross away from the lurking Darren Bent. Just prior to this, a teasing Bentley corner had just evaded Bale and Jonathan Woodgate in the box.
The visitors began to impose themselves later in the half, and arguably ended it the stronger side after Steed Malbranque's 25-yard shot struck Heurelho Gomes' right-hand post on 38 minutes.
It was a sign of things to come, but the first action of the second half came on 48 minutes when Bale missed a great chance to give us the lead, heading a Bentley corner over unmarked from six yards.
Then came a Sunderland onslaught that resulted in them taking the lead. First, Daryl Murphy put a free header over our bar from Andy Reid's free-kick, and the Irish striker was denied by Gomes moments later after getting on the end of El-Hadj Diouf's cross.
But on 54 minutes, we failed to clear our lines on the edge of the box, and former Manchester United midfielder Richardson let fly with an unstoppable 25-yard shot straight into the top corner.
It was a real hammer blow, but the Head Coach responded in positive fashion, bringing both Tom Huddlestone and Giovani Dos Santos off the bench. A flurry of Spurs chances followed.
On the hour, Bentley's in-swinging free-kick from the left took a wicked deflection and was well saved by Craig Gordon, but between them, Bale and Woodgate just couldn't force in the rebound.
The following minute, Jenas headed over a Huddlestone cross and Bent hit the side-netting of Gordon's goal just after that having been released by Bentley.
On 70 minutes, it was Bentley who turned poacher with an excellent 25-yard effort that was well tipped over by the Scottish goalkeeper.
But it was only a matter of time, and two minutes later, a persistent run and shot from Luka Modric forced another save from Gordon, only for Jenas to tap home the rebound and put Spurs back on level terms.
At this point, it looked as if we were favourites to go on and take all three points, with Bentley again forcing Gordan to dive full-stretch to his left and keep out a 30-yard-free-kick.
But in our determination to look for the winner, we left ourselves exposed at the back, and Sunderland took advantage eight minutes from time.
Murphy's cross from the left was headed home by Cisse at the back post to make it a dream debut for the French striker, who arrived on a season-long loan from Marseilles during the week.
With our energy spent, there was no coming back from this, and a hard week's work lays ahead for the team in preparation for what has become a massive game next weekend.
Spurs (4-2-3-1) Gomes; Zokora, Woodgate, King (c), Assou-Ekotto (Huddlestone, 55); Jenas, Modric; Lennon (Giovani, 55), Bentley, Bale; Bent
Subs: Cesar, Gunter, Dawson, Gilberto, O'Hara
Sunderland (4-4-2) Gordon; Bardsley, Nosworthy, Collins, Higginbotham; Malbranque, Whitehead (c), Richardson (Cisse, 65), Reid; Diouf, Murphy
Subs: Ward, Leadbitter, Miller, Chopra, Healy, Stokes