SOUTHEND United suffered late heartache to lose a thrilling FA Cup tie 4-3 against Charlton Athletic at Roots Hall.
The Shrimpers fought back from 2-0 and 3-1 down to take the first round tie to extra time in front a crowd of close to 9,000 fans.
But, just seconds before a penalty shoot-out, Charlton bagged a dramatic late winner with substitute Gassan Ahadme capitalising on a defensive mishap to score.
Before the late drama unfolded, Blues striker Bim Pepple sent an early long range straight at Charlton goalkeeper Will Mannion before Nathan Ralph sent a 30 yard effort wide of the right post.
But, with nine minutes on the clock, Charlton went in front as a left wing cross from Josh Edwards found the head of Miles Leaburn who scored with a well-taken looping header high into the left hand corner of the net.
The Shrimpers hit back with Jack Bridge curling a 20 yard shot straight at Mannion before the Addicks keeper easily held an curling free-kick from James Morton.
With play switching back to the other end of the field, Allan Campbell soon sent a shot wide of the right post from the left hand side of the penalty area.
But, after surviving the scare, the Shrimpers wasted a huge chance to draw back level when Adam Crowther fired over the crossbar from eight yards after the Charlton defence had failed to deal with a left wing cross from Morton.
Moments later, Morton fired over from 25 yards before the visitors doubled their lead five minutes before the break when Terry Taylor’s left wing free-kick found Zach Mitchell who headed home at the far post.
Charlton came within a whisker of making it 3-0 in the 44th minute when Harry Taylor’s slip created a huge chance for skipper Matty Godden.
Taylor was fortunate to avoid punishment for handling the ball on the floor but, with play continuing, Godden raced clean through on goal only to smash his shot against the underside of the crossbar.
Luke Berry fired the rebound over the crossbar but, within seconds, the Shrimpers were back in the game as Oli Coker’s right wing cross was handled the penalty area.
Referee Darren Drysdale pointed to the spot, enabling Jack Bridge to confidently step forward and score with a central effort from 12 yards.
The Shrimpers stayed on the front foot at the start of the second half with Macauley Bonne volleying wide of the right post.
Coker’s half-volley was then held by Mannion but Blus were not to be denied and drew back level in the 52nd minute when Coker netted with a deflected effort from 10 yards.
The Shrimpers soon came close to taking the lead with Gus Scott-Morriss seeing his header impressively kept out by Mannion but Charlton stood firm and regained the lead in the 66th minute with Godden converting from close range.
Blues immediately made a double change with Josh Walker taking the place of Pepple and Cav Miley coming on for Morton in midfield.
Two more alterations soon followed with George Moncur replacing Coker and the fit-again Danny Waldron taking the place of Bonne further forward.
But Southend kept pushing forward and were dramatically rewarded three minutes into stoppage time when Walker’s low, left footed shot was diverted into the back of his own net by Josh Edwards to take the tie to extra time.
At the start of the additional 30 minutes, Walker fired over from 20 yards before Charlton wasted a good chance to regain the lead when Godden was denied by Andeng Ndi from close range.
But, right at the death, the Addicks netted a late winner as a back-pedalling Taylor heading the ball away from his own goalkeeper Andeng Ndi.
The Shrimpers shot-stopper rushed to try and close Ahadme down but the striker turned and fired home to finally see off their spirited hosts.
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