It was a second sickener in seven days.
Charlton threw everything they could possibly muster at Birmingham City, dominating the game from start to finish but came away with nothing to show for their quite valiant efforts.
Federico Macheda was the administrator of the pain as he doubled up with two goals against the run of play, his second coming towards the end as The Addicks poured forward in search of an equaliser.
But the second Blues goal hit Chris Powell and his players hard as the Midlanders stole the points in gut-wrenching fashion.
There were three new faces in the starting XI who were making their first appearances at The Valley. Astrit Ajdarević and Yohann Thuram-Ulien were finally allowed to experience the surroundings of SE7 while Reza Ghoochannejhad looked to introduce himself to the Valley faithful after his impressive turn against Wigan Athletic seven days earlier.
Elsewhere, Loic Négo moved to the bench for Lawrie Wilson who returned after serving his one-match ban while Polish U21 international Piotr Parzyszek took his place amongst the substitutes.
And after a solid full debut at the DW Stadium, Diego Poyet kept his place in Powell's starting XI to be given his home Addicks debut.
It was the first glimpse Charlton fans had of their team in SE7 for 41 days and with some heavy rain falling before kick-off concerns, as always, were abound over how the surface would play.
But both sides tried to play along the ground in the opening exchanges.
Early on the Addicks looked to put Ghoochannejhad through as he tried to get on the end of Ajdarević's measured through-ball, but the Iranian was bundled to the floor in the chase.
There were optimistic cries of 'penalty' around The Valley but, in truth, Blues defender Will Packwood did well to shield his opponent.
At the other end, a Birmingham set-piece routine saw Lee Novak flick an effort into the side-netting.
It was a good, competitive start from both sides who refused to let the boggy pitch stand in the way of good football.
Marvin Sordell flicked on for Ajdarević in the 10th minute but the Standard Liege loanee could only lob well over from the edge of the box. Then, the midfielder had an even better chance.
With Richard Wood heading a long free-kick back into the mixer Ajdarević had space, and time, to send an effort goalward. But his header did not meet the power required as former Addick Darren Randolph collected safely.
Charlton had started brightly, but gloom would soon follow on 22 minutes when the visitors went ahead against the run of play.
When Birmingham won a free-kick on the right flank Emyr Huws stepped up to swing in a left-footed delivery. Federico Macheda was the man who rose highest, directing a header past Thuram-Ulien from 10 yards and into the bottom left-hand corner.
The goal interrupted the Addicks momentum and put a sting in Birmingham's game.
Thuram-Ulien prevented a second when he saved well with his feet in the 29th minute. With Huws splitting the home defence in half with a ball from halfway Chris Burke was in one-on-one.
But the French stopper got out immediately as the ball was cleared to safety.
Charlton had to weather the Birmingham storm but just after the half-hour mark they would find their feet again.
Great build-up play saw Ghoochannejhad do well to lay the ball off to Ajdarević. And Charlton's number 42 showed good vision as he slotted in Jordan Cousins to his right.
But as the academy product bared down on goal with only Randolph to beat, he shot straight at the Irish international's legs.
A glorious chance to draw level had passed the Addicks by but, with heads still up, they kept going.
Ajdarević was again involved in the 37th minute when he delivered an eye-catching, acrobatic volley from Cedric Evina's cross, forcing Randolph into a save.
And the Birmingham stopper kept his side in it a minute later when he flew to his left to keep Johnnie Jackson's volley from creeping inside the post.
Birmingham were well and truly on the back foot as the Blues' defence put themselves in the way of the Addicks' barrage.
On the stroke of half-time Cousins flashed in a cross from the right with Ghoochannejhad busting a gut to get on the end of it.
But he was inches away from a connection as his side retreated for half-time in the ascendency.
Despite being behind there was plenty to be confident about ahead of the second period.
With Poyet looking strong in the middle and Ajdarević pulling the strings peeling off from the left, Charlton looked dangerous going forward and with Ghoochannejhad proving to be a constant handful, there were certainly plenty of positives to take.
And Powell's men emerged after the break in similar vein.
Charlton continued to take the game to Birmingham and with 53 minutes gone Ghoochannejhad came close.
Picking up possession 25 yards from goal he shimmied past a Blues defender before unleashing a shot. But with Packwood getting a foot in the way, the ball looped up and very nearly caught out Randolph who parried it away from dipping under the bar.
The Londoners simply did not deserve to be behind but they had to hit the target.
Michael Morrison curled an effort over when Wilson's cross fell at his feet in space at the back stick when he, perhaps, should simply have squared it or drilled a shot low.
Charlton were knocking and knocking on Birmingham's door and the Valley faithful kept in good voice as they remained hopeful for an answer.
Ghoochannejhad was in again on 62 minutes when he rounded the keeper but with the box busy with blue shirts his effort back across goal from the angle was gobbled up while Sordell's speculative effort from range five minutes later saw Randolph sprawling to his left to make a save.
The Addicks very nearly shot themselves in the foot moments later when Evina let in Burke.
The left-back swung and missed as he attempted to clear his lines, but Thuram-Ulien got his teammate out of jail saving well at his near post.
It was Blues' only sight of goal all half as Charlton went back in search of that elusive equaliser.
Ajdarević fizzed a powerful free-kick from 30 yards which had Randolph worried as he got behind it and that was closely followed by a double switch which saw Simon Church and Danny Green enter the fray in place of Sordell and Jackson with 17 minutes left to play.
With 76 minutes on the clock Ghoochannejhad made another shout for a penalty.
Turning in the box to squeeze between two Birmingham defenders he hit the deck and looked to the referee in hope.
But Mr Adcock shook his head and brandished the Iranian with a yellow card, much to the Covered End's disgust.
Charlton were giving it everything they had in absolute spades, which made what happened next all the more sickening.
Birmingham went on the counter attack in the 79th minute as Tom Adeyemi drove through the midfield.
With the ball teed up for Macheda six yards from goal all the striker had to do was tap in for his brace and kill the Addicks off.
It was a sickener. A sucker-pinch and a complete blow to the gut of the battling men in red.
A goalmouth scramble ensued with six minutes left on the clock as the ball ricocheted off Morrison to go narrowly over the crossbar.
Charlton's stuffing was well and truly knocked out of them and they did not deserve it.
The reality was that it was another defeat as the Addicks remain in the bottom three.
But there are positives to be take from this gut-wrencher of a Saturday afternoon.
Charlton performed well,make no mistake, and with January's new arrivals showing plenty of promise it is important to remember that this fight for Championship survival is far from over.
Charlton: Thuram-Ulien, Wilson, Evina, Morrison, Wood; Jackson (Green 73), Cousins, Poyet (Parzyszek 87), Ajdarević; Sordell (Church 73), Ghoochannejhad.
Subs (not used): Phillips, Hughes, Négo, Lennon.
Booked: Morrison 45 (foul on Lee), Ghoochannejhad 76 (diving)
Birmingham: Randolph; Caddis, Robinson, Martin, Packwood; Lee, Huws; Burke, Adeyemi, Novak; Macheda (Lovenkrands 87).
Subs (not used): Doyle, Blackett, Howard, Brown, Shinnie, Rusnak.
Booked: Huws 71 (foul on Poyet), Macheda 80 (excessive celebration), Robinson 90 (foul on Green).
Goals: Macheda 22,79
Ref: J Adcock
Att: 15,878 (2,001 from Birmingham)