Late heartbreak for Blues in a terrific Fa Youth Cup clash at Roots Hall.
A terrific battling performance from Southend United's under-18s saw Ricky Duncan's side suffer a heartbreaking late defeat against Middlesbrough at Roots Hall, as the visitors earned a 4-3 win in a thrilling game
Southend thought they bagged a 90th minute winner thanks to Nico Cotton's pearler, however, strikes from Dael Fry and then Ben Hetherington sealed the victory for Boro in stoppage time.
Cotton slammed home in the final minute following a terrific run, leaving Boro 'keeper Aynsley Pears with no chance with his screaming effort into the top corner.
Late first half goals from Jordan Williams and Freddie Gard drew Blues level after Boro raced into an early two-goal lead.
However, make no mistake about it, this Blues side showed their resilience and determination against a high flying Boro side, who sit top of their division, above the likes of Manchester United and Manchester City.
It was an encouraging start from the young Blues, but the visitors went ahead with their first attack of the game.
Good wing play from the lively Harry Chapman saw him beat his man, ghost past another before putting the ball into the bottom corner after only six minutes.
Blues' cause wasn't helped as Macauley Keating picked up an injury and had to be substituted four minutes later, with Joe Bedford coming on for the midfielder.
And it was 2-0 after just 25 minutes, with that man Chapman beating the offside trap to poke the ball through the legs of the onrushing Josh Bexon.
But Bexon did excellently just moments later, denying Hetherington's drive from just outside the box.
Blues got earned themselves a lifeline just after the half an hour mark. A deep cross from Williams deceived Pears and after hitting the post, the ball crossed the line to bring Blues back to within a goal of their opponents.
And five minutes before half time, Duncan's side grabbed the equaliser. A good run from Brandon Scott resulted in a strike on goal, and after Pears failed to hold the initial effort, Freddie Gard pounced to get a toe on the ball and put it over the line.
After the break, Blues looked the more likely side to grab a third goal, and Pears had to produce a stunning save to deny a stinging effort from George Burton from all of 20 yards.
With 18 minutes remaining, Bexon did excellently to block a terrific run and strike from the impressive Chapman, as the visitors upped the tempo.
Boro were beginning to turn the screw and on the 80 minute-mark, Bexon did excellently again to stop Chapman - whose free kick was heading into the corner of the net – as he clawed the ball onto the post, before the danger was cleared.
With a minute of normal time left, Hetherington curled over the bar after another brilliant Chapman run.
But the game wasn't finished, and Blues had one more chance left in them, with Cotton slamming home with less than a minute left
However, Boro hit back almost immediately, with Fry and then Hetherington grabbing two late, late goals to win the game for Boro and earn their passage into the next round, against either Millwall or Newcastle United at home.
Blues: Bexon; Williams, Matsuzaka, Coutts, Adeyeye; Scott, Keating (Bedford, 6), Gard, Johnson, Cotton; Burton, (Wabo, 90)
Unused: Phillips. Macree, Salami, Wabo