Jimmy Floyd Hasselbaink did the damage against us again as we failed to break down Chelsea's resolute defence on Saturday.
We enjoyed no shortage of possession in an encounter that was pulsating in periods, quiet in others, but only had three real chances to show.
The best was headed over by Ledley King just minutes before Chelsea opened the scoring in the first half while Fredi Kanoute and Robbie Keane went close in the second half.
There was also a huge shout for a penalty as Michael Brown's effort clearly struck John Terry on the arm but referee Steve Bennett waved appeals away.
With Jamie Redknapp starting his first game since September - up against his cousin Frank Lampard in midfield - and Mauricio Taricco fit again, David Pleat opted for Michael Brown on the right side of a 4-4-2 with Keane and Jermain Defoe up front. Fredi Kanoute was back on the bench.
Defoe, Taricco and Lampard all had pot shots from distance as the game started at pace.
Keane of all people hacked Hasselbaink's header off the line but it remained a case of 'almost, but not quite' in terms of creating chances at both ends until the 35th minute.
That's when arguably our best chance of the afternoon fell to King, darting between defenders to meet Ziege's pinpoint cross only to badly misjudge a free header from 12 yards.
We were punished just two minutes later. Chelsea strung a few passes together for the first time, freeing up Damien Duff in the box and his perfect cross was dispatched by Hasselbaink.
Keane had a chance just before the break, released by Ziege, he sprinted into the box but a tame shot was saved by Marco Ambrosio.
Fredi Kanoute replaced Christian Ziege, struggling with a groin problem, at half-time and went up front with Defoe, Keane moving to the left.
The second half started slowly but came alive again when Brown cut in from the right and crashed a shot goalbound only for Terry to block it with his right arm. It was one of those decisions that are sometimes given - people will say he couldn't get out of the way - but the arm certainly appeared to move towards the ball. Anyway, it was over in a flash and all appeals were ignored.
Keller did well to deny Lampard and then a blow for Redknapp - floored by, off all people, his cousin Lampard in an accidental collision on half-way. Redknapp fell to his knees, blood pouring from a nasty mouth wound. He was desperate to continue but the blood flow couldn't be stopped and he was replaced by John Jackson.
Our play started to get a little ragged as we desperately searched for an equaliser.
Defoe forced Ambrosio to tip over but then another controversial incident as Keane managed to trick his way past two defenders but went to the floor with Terry at his back. Penalty appeals were waved away again and as play continued, the ball fell kindly to Kanoute but he could only muster a tame shot straight at Ambrosio.
A host of substitutions hit the flow of the game in the final quarter and with Chelsea dangerous on the break, we carved out one more chance.
The clock had ticked into injury time when Jackson hit a deep cross headed back by Gardner for Keane to attempt a flying volley that sailed over.
MINUTE BY MINUTE GUIDE
2mins: First effort at goal, Defoe, left corner of box, curler taken well by Ambrosio.
8mins: Taricco tried his luck from 30 yards, always rising.
12mins: Tricks from Keane but cross just too high for Brown at far post.
13mins: Lampard faked to shoot, took two defenders out of the game, eventually blasted wide from 25 yards.
18mins: Doherty crucial defensive header away from Hasselbaink after Parker robbed Taricco.
19mins: OFF LINE. Hasselbaink header from 14 yards hacked away by Keane.
22mins: Decent move, Brown into Defoe, quick spin and shot straight at Ambrosio.
29mins: Wonderful pass from Keane almost released Carr on goal but Carr couldn't take pass in.
35mins: CHANCE. Pinpoint Ziege cross found King in box, 10 yards out, tried to go for the top corner and missed the target.
37mins: GOAL. First decent move from Chelsea freed Duff in box, left side, cross tapped home by Hasselbaink. 0-1.
39mins: Ziege released Keane on half-way, sprinted all the way into the box, low effort saved by Ambrosio's feet.
43mins: Low cross from Carr left by Gallas, Keane taken by surprise and not in position to get anything on it.
45mins: Wicked cross from Ziege deflected away from Defoe by Gallas' desperate lunge.
Half-time: Spurs 0, Chelsea 1
Half-time: Kanoute for Ziege.
47mins: Snapshot from Duff, 25 yards out, saved well to his left by Keller.
52mins: PENALTY? Claims waved away as Brown's shot blocked by Terry's arm.
54mins: YELLOW. Blatant trip from Taricco as Hasselbaink burst away, only saving grace was Gardner covering.
56mins: SAVE. Quick-fire one-touch break from Chelsea ended with fine Keller save to deny Lampard from close range.
60mins: SUB. Kelly for Taricco.
65mins: SUB. Jackson for injured Redknapp (nasty gash in mouth).
66mins: Duff 30-yarder always going wide.
69mins: Defoe curler from distance tipped over by Ambrosio.
72mins: Low cross by Melchiot prodded wide by Hasselbaink.
73mins: SUB. Cole for Parker.
76mins: PENALTY?/CHANCE. Keane magic in box, appeared dragged down by Terry but referee waved play on, ball fell to Kanoute who shot tamely at Ambrosio.
77mins: SUB. Gronkjaer for Gudjohnsen.
82mins: YELLOW. Carr for foul on Makelele.
83mins: SAVE. Flying stop from Ambrosio to beat away Gardner's header from Jackson's corner.
85mins: SUB. Crespo for Hasselbaink.
Injury time: CHANCE. Deep cross from Jackson headed back into danger area by Gardner, Keane flying volley over.
Line-ups: Spurs: Keller, Carr, Taricco (Kelly, 60), Gardner, Doherty, King, Brown, Redknapp (Jackson, 65), Ziege (Kanoute, 45), Defoe, Keane. Subs: Hirschfeld, Poyet.
Chelsea: Ambrosio, Makelele, Lampard, Hasselbaink (Crespo, 85), Duff, Gallas, Melchiot, Bridge, Parker (Cole, 73), Gudjohnsen (Gronkjaer, 77), Terry. Subs: Sullivan, Huth.
Referee: Steve Bennett.