An enterprising first half and a promising beginning to the second was undone by a Jan Vertonghen slip followed by a penalty decision that also saw our number reduced to 10. Two late goals very much rubbed salt into the wounds.
Tim Sherwood lined-up in a 4-2-3-1 system with Kyle Walker fit again and on the right of the midfield three and Aaron Lennon supporting Emmanuel Adebayor. Younes Kaboul was back at centre-half, with Jan Vertonghen starting a left-back. Gylfi Sigurdsson also returned on the left.
Samuel Eto'o, a late change for Fernando Torres, who was in Chelsea's original selection, thought he was in on goal in the opening moments and was one on one with Hugo Lloris before taking a tumble. The flag however, was already aloft.
The defence was carved open in the fifth minute when Frank Lampard played in behind Michael Dawson and the ball was switched in the direction of Eden Hazard, who skipped past Lloris and was forced wide before shooting into the side netting.
The warning signs were there and the team quickly needed to adjust to the changes made.
Thirteen minutes in and there was a big chance to silence the home crowd when Bentaleb cantered through to the right of the area and pulled a shot across goal that, while always highly unlikely to trouble Petr Cech, was not far away from the onrushing Lennon and Walker.
The team was bedding themselves into the game effectively as the clock ticked past 20 minutes, with Walker beginning to make inroads down the right, Adebayor dropping deep to increase involvement, while Lennon's work was tireless off the front.
On 23 minutes a Vertonghen cross was cleared by Gary Cahill but only as far as Sandro, who clubbed it back on the volley and it took a strong save from Cech to deny him another goal at Stamford Bridge.
Eto'o shot wide after a driving run just before the half hour mark, but the rest of the half passed off without too much alarm at either end.
Vertonghen chipped over from a good position in the opening moments of the second half as a crowd of 41,598 were settling back into position on what was a cool evening weather-wise in the south west of the capital.
Chelsea changed their cast list with the introduction of Oscar in place of Lampard with Tim sticking to the starting script. Cech warmed his hands early on with a save from a Kaboul header following a Sigurdsson set piece from the right.
Naughton was booked for checking a swift Chelsea counter with Hazard - the third caution of evening following earlier cards shown to Lampard and Bentaleb. Sandro followed swiftly after a lunge to stop Branislav Ivanovic.
The deadlock was broken on 55 minutes in an unlikely fashion. Vertonghen slipped in possession and tried to salvage the situation by prodding the ball back towards goal. All he succeeded in doing was directing the ball into the path of Eto'o, who was able to slide past Lloris and a lunging last-ditch challenge from Dawson and roll into the net.
It was not a deserved deficit and Eto'o gave his team a chance to increase their lead when he went down under a challenge from Kaboul. There didn't appear to be much in the way of contact and Dawson was across to cover, but the referee deemed it a penalty and a red card.
Hazard slotted home the spot kick and at 2-0 down with 10 men, it was an uphill struggle.
Fortune continued not to favour when Dawson signalled his time on the pitch was up with what looked like a hamstring injury - he was replaced by Zeki Fryers. The team that started with three central defenders on the pitch was now down to one recognised stopper in Vertonghen, who was joined by Sandro in the middle.
With a deficit in the score and 10 men on the pitch the final stages became pretty much about damage limitation as Chelsea sought to take advantage.
It was all quiet until the final two minutes when substitute Demba Ba slotted home from close range after Sandro failed to clear Oscar's cross and in the final seconds, Ba tapped home again after intercepting Walker's header home to Lloris.
All in all, an afternoon to forget.
Chelsea: Cech; Ivanovic, Cahill, Terry (c), Azpilicueta; Matic, Lampard (Oscar, 46); Ramires, Hazard, Schurrle (Willian, 66); Eto'o (Ba, 76). Unused subs: Schwarzer, Kalas, Mikel, Salah.
Spurs: Lloris; Naughton, Dawson (Fryers, 72), Kaboul, Vertonghen; Bentaleb, Sandro; Walker, Lennon, Sigurdsson (Paulinho, 60); Adebayor. Unused subs: Friedel, Chadli, Townsend, Kane, Soldado.
Goals: Eto'o (59), Hazard (penalty, 60), Ba (88, 90).
Yellow cards: Chelsea - Lampard, Azpilicueta. Spurs - Bentaleb, Naughton, Sandro.
Red cards: Spurs - Kaboul.
Referee: Mr M. Oliver.