To make this depressing evening worse, the damage was done by the misfortune of an own goal, as an early Wolves corner cannoned into the net via Jose Bosingwa, who had been recalled to the starting line-up.
Chelsea had 86 minutes with which to respond but could find no breakthrough against Mick McCarthy's tenacious home side, though Salomon Kalou and Florent Malouda both had chances to level in the second half.
The Blues were beginning a game outside the top four for the first time this season, owing to Aston Villa's late equaliser at Stamford Bridge on Sunday, and would also finish the game outside it after a sixth successive away league game without victory.
Carlo Ancelotti made three changes to the side that had begun that game, with Nicolas Anelka, Jeffrey Bruma and Paulo Ferreira making way for Kalou, Branislav Ivanovic and Bosingwa as we travelled to the West Midlands.
Looking at the form league though, Wolves were above the Blues with three wins in their last six matches compared to our one, and it was the hosts who were quickly in front.
It was the worst possible start for Chelsea, falling behind inside the first five minutes when a corner from Stephen Hunt found its way into the net, this following a save from Petr Cech that had prevented Ronald Zubar striking even earlier.
The last touch looked to have been Bosingwa's, though the home PA awarded the goal to Hunt.
It was just the sort of luck we have been growing accustomed to in recent weeks, but there were at least signs of fight from those in blue.
Bosingwa and Kalou combined as the Ivorian squared across the area, Wolves just clearing behind as Chelsea began to exert pressure, forcing three successive corners without testing home goalkeeper Wayne Hennessey.
Kalou had another effort blocked on the edge of the area, Chelsea, as in other games lately, guilty of taking too long in possession.
In his own half, such hesitation almost cost Malouda when Zubar robbed him shortly before the half-hour mark, feeding returning forward Kevin Doyle, but Cech did well to save from the Irishman.
In response Chelsea finally forced Hennessey into action, diving low to deny Kalou an equaliser and a 50th Chelsea goal. Moments later the keeper could only punch a cross as far as John Terry, but unlike on Sunday the Chelsea captain could not find the net.
Kalou almost found Frank Lampard in the box but Wolves were able to clear as they maintained their lead going into the break.
Chelsea opened the second half as they had ended the first, this time Malouda crossing for Didier Drogba, who could only steer his header back towards the crosser. A minute later the Frenchman picked out Ashley Cole, and the left-back hit the target but shot too weakly to beat Hennessey.
It was a bright start and it should have been enough to see us back in the game. On 51 minutes Lampard played an instinctive back-heel into Kalou's path, just inside the Wolves area, and the wide man should have levelled but instead dragged his left-footed effort a foot past the far post.
Chances of such quality would not be easy to come by, though Malouda sent a decent headed opportunity straight into the goalkeeper's hands just four minutes later.
Wolves gradually started to adapt though and for a five-minute spell looked the more likely to score, forcing Terry into some important hold-up play inside his own half before Chelsea could get back on the front foot once more.
Kalou shot high before Drogba struck the woodwork, turning Richard Stearman before driving low at Hennessey's near post. The ball cannoned away and Wolves could clear.
In reply Hunt bent a free-kick onto the crossbar at the other end, before Malouda produced a carbon copy of Kalou's 20 minutes earlier.
Anelka and Daniel Sturridge were thrown on in an attempt to salvage a result, and it was the youngster who squandered the next chance, slicing wide on his weaker right foot after Cole had crossed to the far post.
There had been enough chances to be out of sight by now yet still it was the home side that led. When Hunt beat the Chelsea offside trap he should have at least tested Cech, but Michael Essien got back in time to tackle and keep Chelsea in the contest.
Gael Kakuta joined the action with 13 minutes remaining, on in place of Malouda as Ancelotti's last throw of the dice.
The youngster showed movement when too many of his team-mates were standing still, but the 19-year-old could make no major impact against a spirited and busy Wolves side.
The defeat means we finish the day where we began it, in fifth place, and probably glad of a break from league duties when Ipswich Town come to the Bridge on Sunday, in the FA Cup third round.
Wolves (4-4-2): Hennessey; Zubar, Stearman, Berra, Elokobi; Jarvis, Foley (c), Edwards, Hunt; Fletcher (Ebanks-Blake 67(Milijas 80)), Doyle (Ward 67).
Unused subs: Hahnemann, Batth, Jones, Doherty.
Goals Bosingwa o.g. 4
Booked
Chelsea (4-3-3): Cech; Bosingwa, Ivanovic, Terry (c), Cole; Essien, Ramires (Sturridge 70), Lampard; Kalou (Anelka 64), Drogba, Malouda (Kakuta 77).
Unused subs Turnbull, Ferreira, Bruma, McEachran.
Goals
Booked Ivanovic 45
Referee Mark Halsey
Crowd 26,432.
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