League One minnows Southend stunned Chelsea with a stoppage-time equaliser to earn a deserved 1-1 draw and a third-round replay.
Salomon Kalou's first-half goal looked to have earned Chelsea a place in the next round until Peter Clarke headed an equaliser from close range in the 90th minute.
Chelsea had dominated the game but paid for a host of squandered chances by allowing an unmarked Clarke to beat Carlo Cudicini with a close-range header.
It was just reward for the Shrimpers who valiantly kept out Chelsea's wave of attacks in a pulsating second half.
But Chelsea's need for a first-class finisher was further underlined after an afternoon when they failed to kill off their lowly opponents.
Chelsea's first attempt in the fifth minute was lamentable with Frank Lampard sending a 30-yard free-kick well wide of the target.
Drogba should then have put the Blues ahead in the 10th minute but he waited too long to shoot and former Chelsea youngster Anthony Grant managed to get in a superb tackle to deny the Ivorian.
Lampard then fed Joe Cole inside the penalty area but the England international's shot fizzed across the face of the goal and beyond the far post.
In the 14th minute, another Lampard effort from the edge of the penalty area was deflected to safety but the Shrimpers were living dangerously.
But despite their possession, Chelsea were unable to find a chink in the Southend rearguard.
United defender Clarke had to be alert to stop a low cross from Ashley Cole reaching Drogba in the 20th minute and Kalou wasted a clear chance by shooting over from 20 yards seconds later.
Chelsea continued to pile on the pressure and when Lampard found the rampaging Ashley Cole in the 22nd minute, a goal seemed the only eventuality.
However, the England left-back's right-foot shot from 12 yards was saved by Steve Mildenhall and moments later Drogba placed a shot wide with just the United goalkeeper to beat.
Chelsea continued to dominate and eventually opened the scoring in the 31st minute when Kalou rose unmarked to head home a corner from Lampard.
Three minutes later Drogba could not find the power to beat Mildenhall with a close range header after Ashley Cole had set him up with a cross to the near post.
The goal had enabled Chelsea to with go about their work with calmness but their attempts to increase the scoreline from set pieces were woeful in the extreme.
Juliano Belletti decided it was his turn to try his luck from long-range in the 38th minute but his effort was caught by a surprised onlooker in the second tier of the 'Shed' stand.
Southend had enjoyed little success in attack but a cross from Jean-Francois Christophe had to be turned over his own crossbar by Branislav Ivanovic in the 39th minute.
It was a rare moment of panic in the Chelsea defence and moments later they were back in attack.
But once again their finishing lacked the required quality and Belletti was again guilty of sending his 20-yard effort high and wide.
Southend were unlucky two minutes before the interval when Junior Stanislas made Paulo Ferreira look distinctly ordinary with a great run down the left flank.
However, his low cross into the six-yard box was cleared by a relieved Chelsea defence.
In the 52nd minute Drogba brought a fine save out of Mildenhall when he met a cross from John Obi Mikel.
Chelsea continued to push for a second and Mildenhall was forced to punch clear off the head of Ricardo Carvalho in the 63rd minute.
There was little respite for Steve Tilson's side but they continued to defend valiantly inside their own penalty area.
In the 66th minute Belletti saw his header cleared off the goal-line as the Premier League side searched in vain for a second.
Southend were beginning to show some attacking desire as the game wore on but they were restricted to the odd counter-attack.
The Premier League side pushed the ball around with confidence but their cutting edge was well below par.
In the 82nd minute, Lampard endeavoured to put the game beyond Southend but his 20-yard lob was straight at Mildenhall.
Chelsea then had a narrow escape a minute later when a cross from Johnny Herd was met by Clarke under pressure from Cudicini. The United defender got to the ball first but his header bounced off the top of the crossbar to Chelsea's relief.
But worse was to follow when defender Clarke stunned Chelsea with a 90th-minute equaliser from close range.
Chelsea were denied a late winner by Mildenhall when he somehow kept out a header from substitute Franco Di Santo.
Scolari wants more concentration from Blues
Chelsea boss Luiz Felipe Scolari hinted that his players were suffering a crisis of confidence in front of goal after League One minnows Southend snatched a last-gasp draw at Stamford Bridge. Chelsea's front three of Joe Cole, Didier Drogba and goalscorer Salomon Kalou cost almost £40million to assemble and yet they squandered another hatful of chances to kill off their lowly opponents.
The Blues were guilty of the same offences when Championship side Burnley bundled them out of the Carling Cup on penalties and the Brazilian's post-match lament is becoming all-too familiar.
''I need to teach to my players more concentration when they arrive in front of goal,'' said a disappointed Scolari.
''This is my job every day.
''Maybe it is confidence when they arrive in front of goal, maybe pressure. They need to score more goals and get more confidence. Only this.
''If they are not together, they would not create 15 chances. We played very well and created 15 chances but only one goal.
''Southend played hard and very spirited for a draw. They got a draw but only had one shot on goal.
''Carlo Cudicini didn't make one save. Not scoring is our mistake. All the players feel the same as me.''
But Scolari reiterated that he will not buy a new striker and pledged to work harder on the training ground instead.
''We need to follow the same ideas - train, train, train,'' said Scolari. ''I don't need another striker. I have a good squad, good players.
''We are still in the cup. Other teams that lost today are out, we are not out. We were better than Southend but didn't score a second goal.''
Southend rejoiced in Clarke's equaliser and will now look forward to another pay-day in the replay at Roots Hall.
United boss Steve Tilson was understandably delighted with the outcome.
''It's a fantastic day for the club and fans,'' said Tilson.
''We had to ride our luck and we got the chance at the death.
''Our goalkeeper made a great save at the end to keep us in it but the idea was to stay in the game for as long as we could.
''We had to get a lot of bodies behind the ball and it is not how we normally play. But it worked wonders.
''But whatever happens, we have had a good cup run. Beating Crewe at home in the league in our next game is more important than Chelsea.
''We have not worked on the long throws from the right-hand side so that was a bonus.
''Peter does get in good positions and that is his second goal this season. But on another day we could have lost by four or five goals.
''If they had scored early on then we would have had to open up and possibly got beaten by a hatful.
''But it is a great result for us against a team that will finish in the top two of the Premier League I'm sure.''
Chelsea have sold Wayne Bridge to Manchester City for a reported £12 million.
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