League Two side Southend United claimed a shock away win against Leyton Orient in the first leg of the Johnstone's Paint Trophy southern area final.
Ryan Leonard scored the winner when he flicked the ball into the net from Sean Clohessy's low right-wing cross.
The hosts had numerous chances but Shrimpers goalkeeper Paul Smith made a series of fine saves to deny Lee Cook, Dave Mooney and Shaun Batt.
Mooney also hit the bar in injury-time but Southend held on for the victory.
The Shrimpers now hold a one-goal advantage ahead of the second leg at Roots Hall in a fortnight's time and the winners will advance to the Wembley final on Sunday, 7 April.
Sturrock bids for Wembley
Southend United boss Paul Sturrock was taking charge of his 150th game as manager of the Essex side.
He has been a manager for 879 games in his career, but he is yet to lead a team out at Wembley.
League One Orient started brightly in front of their highest home crowd of the season of 5,359 and had the best chances of the first half.
However, Smith held on to a Cook free-kick, saved Mooney's close-range volley and parried two efforts from Batt, who was making his home debut after joining the O's on loan from Millwall last week.
Orient's misses proved costly as the Shrimpers, the lowest-ranked side left in the competition, took a 57th minute lead.
Michael Timlin released the overlapping Clohessy and his deflected cross fell to Leonard, who bundled the ball home at the near post from close range.
Southend's Kevan Hurst missed a chance to double the visitors' lead, shooting narrowly wide from the edge of the penalty area.
But Mooney should have levelled the game when he wasted two opportunities. He lifted the ball over the crossbar when he only had Smith to beat and then fired against the bar from close range late on.
However, Southend's victory was overshadowed by an injury to Timlin, who was carried off on a stretcher in the second half.
The eventual winners of this game will face either Coventry or Crewe at Wembley, with Crewe holding a 3-0 lead after the first leg of the northern final.
VIEW FROM THE DRESSING ROOM
Southend United manager Paul Sturrock told BBC Essex:
"I'm gutted for him [Michael Timlin], it's a suspected broken leg. It does look bad.
"I'm really disappointed, the lad's been a stalwart for us. He has his good days and his bad days but he wears his heart on his sleeve. I'm just absolutely gutted, it's put a dampener on the night.
"It was a difficult game. We decided that we would play nice and tight and solid. The start of the second half was excellent, for about half an hour we got ourselves in the right areas.
"I hope it doesn't cause complacency - they've got some players that can hurt us."
Live Text Commentary
Full Time The match has reached full-time.90:00 +9:25
The referee gives a free kick against Dean Cox for handball. Paul Smith takes the indirect free kick.90:00 +8:06
Kevan Hurst decides to take a short corner.90:00 +6:39
Mathieu Baudry concedes a free kick for a foul on Chris Barker. Direct free kick taken by Paul Smith.90:00 +6:19 Substitution
Substitution Caolan Lavery replaces Ben Reeves.90:00 +5:52
Outswinging corner taken right-footed by Dean Cox played to the near post, clearance made by Chris Barker.90:00 +5:40
Outswinging corner taken right-footed by Dean Cox from the right by-line, Mark Phillips manages to make a clearance.90:00 +5:18
Lee Cook crosses the ball, David Mooney takes a shot. Paul Smith makes a save.90:00 +4:44
Ryan Leonard gives away a free kick for an unfair challenge on Mathieu Baudry. Free kick taken by Lloyd James.90:00 +4:07
Moses Odubajo sends in a cross, David Mooney takes a shot.90:00 +0:48
Corner taken right-footed by Dean Cox from the left by-line to the near post, Ryan Cresswell makes a clearance.90:00 +0:32
Inswinging corner taken by Lee Cook from the right by-line, Mark Phillips manages to make a clearance.90:00 +0:15 Booking
Booking Chris Barker goes into the book for unsporting behaviour.90:00 +0:09 Booking
Booking Dean Cox receives a yellow card for unsporting behaviour.89:37
Moses Odubajo takes a shot. Save made by Paul Smith.88:47
Inswinging corner taken by Dean Cox from the left by-line, clearance made by Alex Woodyard.88:31
Afolabi Obafemi takes a shot. Blocked by Sean Clohessy.87:04 Substitution
Substitution Barry Corr comes on in place of Britt Assombalonga.86:42 Substitution
Substitution Afolabi Obafemi joins the action as a substitute, replacing Shaun Batt.86:27 Substitution
Substitution (Southend) makes a substitution, with John Spicer coming on for Michael Timlin.
The ball is sent over by Dean Cox, clearance by Ryan Cresswell.80:02
Free kick taken by Dean Cox.80:02 Booking
Booking Michael Timlin goes into the book for time wasting.79:48
Unfair challenge on Shaun Batt by Ryan Cresswell results in a free kick.79:03
Effort on goal by David Mooney from inside the penalty area goes harmlessly over the bar.75:33
Free kick awarded for an unfair challenge on David Mooney by Mark Phillips. Direct free kick taken by Lee Cook.73:44 Substitution
Substitution Jimmy Smith is brought on as a substitute for Martin Rowlands.73:44
Lee Cook takes a inswinging corner from the right by-line played to the near post.69:33
Foul by Kevan Hurst on Martin Rowlands, free kick awarded. Jamie Jones restarts play with the free kick.69:19
Centre by Ryan Leonard, Chris Barker makes a clearance.68:14
Dean Cox crosses the ball from the free kick right-footed from left wing, clearance by Ryan Cresswell.68:14 Booking
Booking Sean Clohessy goes into the referee's book.68:08
Free kick awarded for a foul by Sean Clohessy on Shaun Batt.67:33
Free kick awarded for an unfair challenge on Mathieu Baudry by Britt Assombalonga. Mathieu Baudry takes the free kick.67:05
The ball is swung over by Moses Odubajo.66:26
Dean Cox crosses the ball, Ryan Cresswell manages to make a clearance.64:54
Paul Smith takes the direct free kick.64:54 Booking
Booking The referee shows Shaun Batt a yellow card.64:42
Michael Timlin fouled by Shaun Batt, the ref awards a free kick.64:22
Alex Woodyard takes a shot. Scott Cuthbert gets a block in.62:27
Kevan Hurst has an effort direct from the free kick.62:27 Booking
Booking Martin Rowlands booked.62:11
Martin Rowlands challenges Alex Woodyard unfairly and gives away a free kick.61:35
Ben Reeves fouled by Martin Rowlands, the ref awards a free kick. Kevan Hurst takes the free kick.60:48
Effort from outside the box by Kevan Hurst hits the post.59:38
Free kick awarded for a foul by Britt Assombalonga on Mathieu Baudry. Jamie Jones takes the direct free kick.58:57
Shaun Batt takes a shot from just inside the penalty box which clears the crossbar.57:03
The ball is swung over by Sean Clohessy,56:57
The assist for the goal came from Sean Clohessy.56:57 Goal scored
Goal! - Ryan Leonard - Leyton O 0 - 1 Southend Ryan Leonard scores a goal from inside the six-yard box to the bottom left corner of the goal. Leyton Orient 0-1 Southend.56:38
Outswinging corner taken right-footed by Kevan Hurst from the right by-line.56:08
Centre by Britt Assombalonga, Kevan Hurst takes a shot. Mathieu Baudry gets a block in.55:27
Lee Cook takes a shot. Paul Smith makes a save.54:18
Britt Assombalonga takes a shot from just inside the penalty box which clears the crossbar.53:44
Shaun Batt challenges Mark Phillips unfairly and gives away a free kick. Ryan Cresswell takes the free kick.52:56
Foul by David Mooney on Sean Clohessy, free kick awarded. Sean Clohessy takes the direct free kick.51:57
The offside flag is raised against Sean Clohessy. Jamie Jones takes the free kick.50:44
Michael Timlin takes a shot. Blocked by Mathieu Baudry.48:49
The assistant referee flags for offside against David Mooney. Ryan Cresswell takes the indirect free kick.47:45
The ball is swung over by Moses Odubajo.47:04
Dean Cox takes the inswinging corner, save by Paul Smith.45:27
Inswinging corner taken right-footed by Dean Cox from the left by-line, Ryan Cresswell manages to make a clearance.45:18
The ball is swung over by Gary Sawyer, clearance by Ryan Cresswell.45:01
The match restarts for the second half.45:00 +1:10 Half time
Half Time The ref blows to signal half-time.41:26
Ryan Leonard fouled by Moses Odubajo, the ref awards a free kick. Kevan Hurst crosses the ball in from the free kick, save made by Jamie Jones.40:04
Free kick awarded for a foul by Ben Reeves on Lloyd James. Scott Cuthbert takes the direct free kick.39:13
Unfair challenge on Ben Reeves by Martin Rowlands results in a free kick. Ben Reeves fires a strike on goal direct from the free kick.37:46
Shaun Batt takes a shot. Save made by Paul Smith. Lee Cook takes a shot. Mark Phillips gets a block in. Corner taken by Dean Cox, Ryan Cresswell manages to make a clearance.36:37
Corner taken by Dean Cox played to the near post, Chris Barker manages to make a clearance.36:19
Shaun Batt takes a shot. Paul Smith makes a save.36:04
Britt Assombalonga takes a shot. Jamie Jones makes a save.35:20
Dean Cox produces a right-footed shot from close in which goes wide of the right-hand upright.33:48
Free kick awarded for a foul by Scott Cuthbert on Britt Assombalonga. Ben Reeves produces a shot on goal direct from the free kick.32:31
Corner taken right-footed by Kevan Hurst, clearance by Gary Sawyer.31:53
Free kick awarded for a foul by Shaun Batt on Mark Phillips. The ball is sent over by Sean Clohessy, Ryan Leonard takes a shot. Scott Cuthbert makes a clearance.31:19
The ball is swung over by Sean Clohessy, clearance made by Scott Cuthbert.31:07
The ball is crossed by Ben Reeves, clearance by Gary Sawyer.29:41
David Mooney is flagged offside by the assistant referee. Free kick taken by Paul Smith.26:00
Mathieu Baudry concedes a free kick for a foul on Britt Assombalonga. Kevan Hurst crosses the ball in from the free kick, save by Jamie Jones.24:24
Free kick awarded for an unfair challenge on Britt Assombalonga by Mathieu Baudry. Free kick taken by Michael Timlin.22:41
David Mooney takes a shot from just inside the penalty box which clears the crossbar.21:30
Centre by Lee Cook, David Mooney takes a shot. Save by Paul Smith.20:47
The ball is crossed by Kevan Hurst, comfortable save by Jamie Jones.17:55
Michael Timlin concedes a free kick for a foul on Shaun Batt. Lee Cook produces a shot on goal direct from the free kick, comfortable save by Paul Smith.16:18
Corner taken by Dean Cox.16:01
Lee Cook produces a cross, blocked by Ryan Cresswell.15:48
Moses Odubajo sends in a cross.15:10
Handball by Shaun Batt. Paul Smith restarts play with the free kick.14:16
A cross is delivered by Lee Cook, Ryan Cresswell makes a clearance.12:23
Alex Woodyard handles the ball and concedes a free kick. Martin Rowlands takes the free kick.11:51
Shot from just outside the area by Shaun Batt misses to the right of the target.9:26
Inswinging corner taken by Dean Cox, Kevan Hurst manages to make a clearance.7:47
Kevan Hurst sends in a cross. The assistant referee signals for offside against Mark Phillips. Indirect free kick taken by Jamie Jones.6:51
Unfair challenge on Sean Clohessy by Gary Sawyer results in a free kick. Free kick crossed right-footed by Kevan Hurst, clearance by Martin Rowlands.0:00
The referee gets the game started.
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