Blues exited the Emirates FA Cup at the second-round stage as Chris Powell’s side lost 4-2 to Barnsley at Roots Hall.
Kieffer Moore put the visitors in front with his fifth goal in three games against Southend midway through the first-half, powering a header home from an Alex Mowatt corner.
Southend would level though right on half-time when Sam Mantom’s corner appeared to go all the way through and into the back of the net to make it 1-1 at the break.
Barnsley retook the lead early in the second-half when Blues failed to deal with another set-piece from Mowatt, allowing Cauley Woodrow to score from close range.
And the former Southend-loanee would put daylight between the two sides by tapping in Mike Bahre’s cross-come-shot after Blues again failed to deal with a corner.
Southend would give themselves hope of staying in the competition when Timothee Dieng headed in Stephen McLaughlin’s corner before Blues thought they’d equalised in the final minute of normal time only for Michael Turner’s strike to be controversially ruled out for offside.
It didn’t matter in the end though as Barnsley wrapped up the win in the fifth minute of stoppage time after George Moncur’s effort was parried to Bahre who fired in a fourth for the Tykes.
The win for the visitors sees them go into the hat for Monday’s third-round draw while Southend must now concentrate on improving their league fortunes.
Having picked up a morale-boosting win in mid-week against Scunthorpe, high-flying Barnsley were a different proposition entirely to the Iron and Daniel Stendel’s side had already beaten Southend just under a month ago at Oakwell.
After the win against Scunthorpe, Chris Powell tried to freshen things up by making four changes as Elvis Bwomono, Michael Turner, Michael Kightly and Dru Yearwood came in for Jason Demetriou, Taylor Moore, Harry Bunn and Luke Hyam.
With a place in the third round at stake and a chance to face the big boys from the Premier League, both sides took some time to feel each other out in the early stages at Roots Hall with neither team able to find a clear breakthrough early on.
Barnsley would carve out by far the best chance of the half midway through the first period when former Col U player George Moncur slid Kieffer Moore clean through. The Tykes striker beat the advancing Mark Oxley but his shot lacked power, allowing Stephen Hendrie to clear off the line.
The visitors though would take the lead just shortly before the interval with a carbon copy of the goal they scored in the league game between the two sides back in November, with Moore giving the Tykes the lead with less than five minutes remaining in the half.
After Woodrow’s dipping strike forced Oxley to tip the ball wide for a corner, Alex Mowatt whipped the set-piece into the penalty area with Moore planting his header into the back of the net to put Barnsley front.
All signs pointed to Barnsley taking that lead into the interval, but Southend would level in the fourth minute of added on time after Timothee Dieng won Blues a corner. Sam Mantom’s near post ball appeared to go all the way through and into the net to make it 1-1.
The tie was evenly poised going into the second-half and Dieng thought he’d given Southend the lead shortly after the break, nicking the ball beyond Adam Davies to tap in only to see the linesman’s flag had been up for some time for offside against the Frenchman.
Having conceded from a corner in the first-half, Southend’s fragility at defending crosses was again their downfall as Barnsley retook the lead before the hour mark. A Mowatt corner was dropped on the line by Oxley under pressure, allowing Cauley Woodrow the bundle the ball over the line.
The former Southend loanee would then go and score again from another corner with 20 minutes remaining to all but condemn Blues to a second-round exit. After Southend failed to clear a Mowatt set-piece, Mike Bahre’s shot across goal found the run of Woodrow to make it 3-1 with a simple tap-in.
With nothing to lose, Powell made a triple substitution bringing on Harry Bunn, Theo Robinson and Shawn McCoulsky and Blues would get themselves back in the tie with little over five minutes remaining when Dieng headed in McLaughlin’s corner to give Southend hope.
Knowing that another goal for Blues would almost certainly force a replay up in Yorkshire, Southend thought they had equalised in the final minute of normal time when Blues won a corner. After Bunn’s header on goal was saved, Turner rifled home only for the linesman to rule the goal out for offside.
Southend couldn’t believe their bad luck and the decision seemed harsh on the Blues, but it would matter not in the end as Barnsley booked their place in the third round when Mike Bahre fired in from close range late on to send Barnsley into Monday’s draw.
Blues XI: Oxley, Bwomono, Turner, Kightly (Bunn 76’), Dieng, Cox (Robinson 76’), McLaughlin, Yearwood (McCoulsky 76’), Mantom (C), Hendrie, White. Subs Not Used: Bishop, Hyam, Moore, Hutchinson
Barnsley XI: Davies (C), Fryers (Pinillos 68’), Pinnock, Lindsay, McGeehan, Moncur, Moore (Potts 81’), Bahre, Woodrow (Adeboyejo 90+1’), Mowatt, Brown. Subs Not Used: Greatorex, Cavare, Jackson, Thiam
Referee: Paul Marsden
Assistants: Rob Smith & Andrew Ayott
Fourth Official: Sam Purkiss
Southend United: Sam Mantom 45+4’, Timothee Dieng 84’
Barnsley: Kieffer Moore 41’, Cauley Woodrow 56’, 70’, Mike Bahre 90+5’
Southend United: None
Barnsley: Zeki Fryers 45+2’
Attendance: 3,616 (343 Away)