West Brom suffered penalty shoot-out heartbreak as Arsenal triumphed at The Hawthorns in round three of the Capital One Cup.
Craig Dawson and Morgan Amalfitano missed the decisive penalties as the Baggies bowed out 4-3 on spot-kicks after the game ended 1-1 at the end of extra-time.
Thomas Eisfeld had fired a young Gunners side ahead midway through the second half of normal time before Albion young-gun Saido Berahino levelled to take the game into an extra half-hour, which failed to produce another goal.
Luke Daniels made a shoot-out save for Albion but it was the visitors whose nerve held.
Albion had the first sight of goal when Steven Reid, making his first appearance of the season after injury, delivered a first-time cross towards Shane Long at the far post.
Long managed to direct the ball across goal but Per Mertesacker managed to help it back into the arms of grateful keeper Lukasz Fabianksi.
But the first half was a tepid affair with neither side threatening regularly, although Goran Popov tried his luck for the home side with a powerful long-range shot that flew high and wide and into the Smethwick End.
They had another chance when Saido Berahino was fouled and Graham Dorrans’ free-kick reflected behind off the Gunners wall.
And, from the resulting corner, Craig Dawson saw his looping header tipped over by Fabianski.
In first-half stoppage-time Berahino was chopped down again 35 yards out and Reid saw his free-kick clip the crossbar with referee Robert Madley ruling that Fabianski had tipped it over, although Arsenal were furious about the award of a corner.
Early in the second half, Carl Jenkinson went on a jinking run and curled a shot just wide.
But Albion continued to pressurise and they might have opened the scoring when Long delivered a fine cross from the right towards Stephane Sessegnon at the far post but Mertesacker made a crucial interception.
And moments later the Baggies were denied by a brilliant save from Fabianski, who flew to tip over a drive from Youssouf Mulumbu after a good run and cross from the lively Sessegnon.
But the Gunners took the lead 28 minutes from full-time when Mulumbu gave away possession in midfield and the Baggies’ back four switched off, allowing Eisfeld to race onto Nicklas Bendtner’s perfect pass to finish.
However, the Baggies were level 19 minutes from the end through Berahino.
A Dorrans corner drifted beyond the far post but Long kept it alive with a chip that the youngster nodded home.
Extra-time was a relative non-event until the closing moments, when Albion had three fine chances to grab victory.
Firstly, Morgan Amalfitano rattled the crossbar with a powerful shot and then his fellow substitute Markus Rosenberg missed a glorious opportunity.
He received a ball over the top and lobbed Fabianski but, with the ball going wide, chased it down and controlled.
With the goal gaping, he hit a tame shot that was blocked by Mertesacker.
Then a Rosenberg cross was met by Sinclair but he screwed a shot wide.
Albion took a 3-1 lead in the shoot-out as Serge Gnabry’s penalty was saved by Daniels.
But Dawson and Amalfitano missed the target for the Baggies with Nacho Monreal scoring the winning spot-kick.
By Steve Madeley