Macclesfield needed a bizarre stroke of luck in a penalty shoot-out to beat Southend and progress in the FA Cup.
Nat Brown's decisive penalty appeared to be saved by Glenn Morris, but as the keeper celebrated the ball spun into the net to hand the Silkmen victory.
Earlier, Emile Sinclair capitalised on a Peter Gilbert error to round Morris and net, but Josh Simpson volleyed home late on to take it to extra time.
Aristote Nsiala volleyed Town ahead before Barry Corr tapped in to level.
The victory will be especially sweet for Macclesfield, who end their Roots Hall hoodoo to win after six consecutive losses at the Blues' home.
After a quiet opening hour, the game sprung into life when Sinclair took advantage of poor defending by Gilbert, and Nsiala set his team-mate up to put the Silkmen on their way.
An elusive victory seemed assured before Simpson thumped in an equaliser to send the Shrimpers faithful into raptures and force the game into extra time.
But soon after, Nsiala thought he had booked Macclesfield's passage into round two when he hit a stunning volley of his own to restore the advantage.
And at the very end of the first half of extra time, Corr drew the home side level in dramatic fashion to take the match all the way to spot kicks.
The shoot out saw seven converted penalties before hero-turned-villain Corr stepped up and missed from 12 yards.
Southend keeper Morris thought he had saved the day when Brown's effort appeared to be saved, but he was cruelly denied as the Silkmen finally made it through in fortuitous circumstances to set up an away tie at Huddersfield.
Live text and stats
Tuesday, 16 November 2010
The FA Cup
(HT 0-0)Macclesfield win 5-3 on penalties
06 Bilel yellow card
16 Prosser yellow card (German 79)
11 Zaaboub (Hall 62)
25 Midson (Sturrock 62)
15 Bolland yellow card (Draper 112)
09 Sinclair (Mukendi 90)
Ref: WhitestoneAtt: 2,194
Attempts on target
Attempts off target
123:19 Penalty scored by Nathaniel Brown. Southend 3-5 Macclesfield on penalties.
123:00 Ryan Hall scores a penalty. Southend 3-4 Macclesfield on penalties.
122:21 Penalty scored by Izak Reid. Southend 2-4 Macclesfield on penalties.
121:59 Penalty scored by Sean Clohessy. Southend 2-3 Macclesfield on penalties.
121:15 Penalty scored by Hamza Bencherif. Southend 1-3 Macclesfield on penalties.
120:49 Spot kick missed by Barry Corr.
120:28 Tyrone Barnett scores a penalty. Southend 1-2 Macclesfield on penalties.
120:10 Penalty scored by Antonio German. Southend 1-1 Macclesfield on penalties.
120:01 The referee calls the first player forward to start the penalty shoot-out.
120:01 Penalty scored by Lewis Chalmers. Southend 0-1 Macclesfield on penalties.
Extra Time Complete
120:00+0:16 The match goes to a penalty shoot-out.
117:53 Antonio German conjures a left-footed shot from inside the six-yard box that clears the bar.
117:42 Antonio German crosses the ball, Paul Morgan makes a clearance.
117:01 Ross Draper gives away a free kick for an unfair challenge on Anthony Grant. Direct free kick taken by Glenn Morris.
112:16 Foul by Colin Daniel on Blair Sturrock, free kick awarded. Free kick crossed by Ryan Hall.
111:27 Substitution (Macclesfield) makes a substitution, with Ross Draper coming on for Paul Bolland.
111:04 Anthony Grant takes a shot from 30 yards. Save by Jose Veiga.
109:31 Bilel Mohsni takes a shot. Save by Jose Veiga.
108:50 Unfair challenge on Barry Corr by Paul Morgan results in a free kick. Ryan Hall restarts play with the free kick.
107:23 Inswinging corner taken left-footed by Ryan Hall from the right by-line, clearance by Colin Daniel.
106:33 Blair Sturrock is flagged offside by the assistant referee. Jose Veiga takes the free kick.
106:19 Sean Clohessy delivers the ball.
Extra Time Started
105:01 The referee blows his whistle to start the second half of extra time.
Extra Time Half Time
105:00+0:15 GOAL - Barry Corr:Southend 2 - 2 Macclesfield Goal scored by Barry Corr from close in to the bottom right corner of the goal. Southend 2-2 Macclesfield.
104:23 Tyrone Barnett takes a shot. Blocked by Bilel Mohsni.
Correction - 101:10 Aristote Nsiala takes a shot. Save by Glenn Morris.
101:10 Vinny Mukendi takes a shot. Save by Glenn Morris.
100:35 Tyrone Barnett has an effort at goal. Glenn Morris makes a save.
100:15 Centre by Blair Sturrock, Nathaniel Brown makes a clearance.
98:33 GOAL - Aristote Nsiala:Southend 1 - 2 Macclesfield Aristote Nsiala scores a goal from the edge of the penalty area to the top left corner of the goal. Southend 1-2 Macclesfield.
98:20 Lewis Chalmers delivers the ball, clearance made by Sean Clohessy.
97:27 Ryan Hall takes a shot. Paul Morgan gets a block in.
96:16 Antonio German produces a left-footed shot from outside the penalty box and misses left.
95:50 A cross is delivered by Lewis Chalmers, clearance made by Glenn Morris.
95:43 Centre by Tyrone Barnett.
94:53 The ball is swung over by Sean Clohessy, Header from deep inside the area by Antonio German goes over the bar.
91:21 Colin Daniel delivers the ball.
Extra Time Started
90:00+4:53 The whistle goes for the end of normal time.
90:00+4:10 Anthony Grant takes a shot. Blocked by Paul Bolland.
90:00+3:31 Outswinging corner taken by Ryan Hall from the left by-line, Craig Easton takes a shot. Blocked by Paul Morgan.
90:00+2:24 Outswinging corner taken by Lewis Chalmers, Headed effort from inside the area by Vinny Mukendi misses to the left of the
90:00+1:14 Tyrone Barnett fouled by Bilel Mohsni, the ref awards a free kick. The free kick is swung in right-footed by Lewis Chalmers,
save by Glenn Morris.
90:00+1:14 Booking Booking for Bilel Mohsni for dissent.
90:00+0:36 Antonio German handles the ball and concedes a free kick. Jose Veiga takes the free kick.
89:16 Substitution Emile Sinclair goes off and Vinny Mukendi comes on.
88:32 Nathaniel Brown takes a shot. Save made by Glenn Morris.
86:04 GOAL - Josh Simpson:Southend 1 - 1 Macclesfield Josh Simpson gets on the score sheet with a goal from inside the box to the bottom left corner of the goal. Southend 1-1 Macclesfield.
85:42 Sean Clohessy delivers the ball, Jose Veiga manages to make a clearance.
84:43 Hamza Bencherif takes a shot. Save by Glenn Morris.
84:34 Hamza Bencherif takes a shot. Glenn Morris gets a block in.
82:49 The ball is delivered by Sean Clohessy, Jose Veiga makes a clearance.
82:43 The ball is swung over by Ryan Hall.
79:54 Foul by Antonio German on Colin Daniel, free kick awarded. Lewis Chalmers takes the direct free kick.
Correction - 79:00 Substitution Antonio German comes on in place of Luke Prosser.
79:00 Substitution Luke Prosser goes off and Antonio German comes on.
77:54 Blair Sturrock challenges Aristote Nsiala unfairly and gives away a free kick. Izak Reid takes the direct free kick.
77:41 Emile Sinclair takes a shot. Save made by Glenn Morris.
76:50 Foul by Luke Prosser on Emile Sinclair, free kick awarded. Lewis Chalmers takes the direct free kick.
76:50 Booking Luke Prosser is cautioned by the ref for unsporting behaviour.
76:32 Shot by Blair Sturrock. Blocked by Aristote Nsiala.
76:14 Shot by Ryan Hall. Jose Veiga makes a save.
75:35 Unfair challenge on Peter Gilbert by Tyrone Barnett results in a free kick. Direct free kick taken by Glenn Morris.
75:08 Free kick awarded for a foul by Peter Gilbert on Izak Reid. Direct free kick taken by Lewis Chalmers.
72:03 Peter Gilbert sends in a cross, Close range header by Blair Sturrock goes wide of the left-hand upright.
68:36 Foul by Blair Sturrock on Paul Morgan, free kick awarded. Free kick taken by Lewis Chalmers.
67:19 Corner taken by Lewis Chalmers from the right by-line.
67:11 Emile Sinclair crosses the ball, Anthony Grant manages to make a clearance.
66:09 Corner taken right-footed by Lewis Chalmers from the right by-line, Nathaniel Brown takes a shot.
62:41 Corner taken left-footed by Ryan Hall to the near post, Shot by Bilel Mohsni. Save by Jose Veiga.
61:18 Substitution Blair Sturrock on for Jack Midson.
61:18 Substitution Ryan Hall joins the action as a substitute, replacing Sofiene Zaaboub.
60:22 The assist for the goal came from Aristote Nsiala.
60:22 GOAL - Emile Sinclair:Southend 0 - 1 Macclesfield Emile Sinclair fires in a goal from deep inside the penalty box to the bottom left corner of the goal. Southend 0-1 Macclesfield.
59:35 Outswinging corner taken from the right by-line by Lewis Chalmers, Sofiene Zaaboub manages to make a clearance.
59:23 Hamza Bencherif sends in a cross, Luke Prosser manages to make a clearance.
58:39 Sean Clohessy sends in a cross, save by Jose Veiga.
56:22 Shot on goal by Barry Corr from inside the box goes harmlessly over the target.
55:17 The ball is sent over by Sofiene Zaaboub, Craig Easton takes a shot. Hamza Bencherif gets a block in.
54:22 Effort from the edge of the box by Emile Sinclair goes wide of the left-hand upright.
53:27 Sofiene Zaaboub sends in a cross, save made by Jose Veiga.
52:09 Shot by Craig Easton. Blocked by Lewis Chalmers.
51:12 A cross is delivered by Sofiene Zaaboub.
51:07 The ball is delivered by Sofiene Zaaboub, clearance by Izak Reid.
50:36 Effort on goal by Emile Sinclair from inside the penalty box misses to the right of the target.
49:34 Emile Sinclair takes a shot.
48:50 Lewis Chalmers takes a inswinging corner from the left by-line to the near post, clearance made by Sean Clohessy.
48:35 Paul Bolland sends in a cross, Hamza Bencherif takes a shot. Blocked by Sean Clohessy.
48:10 Barry Corr takes a shot. Jose Veiga makes a save.
47:51 Free kick awarded for an unfair challenge on Anthony Grant by Lewis Chalmers. Luke Prosser takes the free kick.
45:01 The game restarts for the second half.
45:00+1:21 The ref blows to end the first period.
44:53 Shot by Sofiene Zaaboub from outside the box goes over the net.
43:07 Corner taken by Sofiene Zaaboub, Header from deep inside the area by Luke Prosser goes harmlessly over the crossbar.
42:29 Unfair challenge on Sofiene Zaaboub by Paul Bolland results in a free kick. The ball is crossed by Sofiene Zaaboub, Luke Prosser
takes a shot. Save made by Jose Veiga.
39:20 Foul by Aristote Nsiala on Jack Midson, free kick awarded. Sofiene Zaaboub crosses the ball from the free kick left-footed
from left channel.
38:38 Sofiene Zaaboub fouled by Paul Bolland, the ref awards a free kick. Direct free kick taken by Glenn Morris.
38:38 Booking The referee cautions Paul Bolland for unsporting behaviour.
36:16 Colin Daniel takes a shot. Save by Glenn Morris.
33:54 Jack Midson is caught offside. Indirect free kick taken by Lewis Chalmers.
30:51 Sofiene Zaaboub sends in a cross, save made by Jose Veiga.
29:14 Shot from just outside the box by Izak Reid misses to the right of the goal.
28:37 Shot by Barry Corr from 25 yards. Blocked by Nathaniel Brown.
27:33 A cross is delivered by Sofiene Zaaboub.
25:15 Shot from long range by Izak Reid misses to the right of the goal.
24:36 The ball is crossed by Peter Gilbert, Bilel Mohsni has a headed effort at goal from close in which goes wide right of the
24:15 Corner taken left-footed by Sofiene Zaaboub from the left by-line to the near post, Hamza Bencherif makes a clearance.
24:07 Josh Simpson produces a cross, Colin Daniel gets a block in.
23:04 Foul by Hamza Bencherif on Luke Prosser, free kick awarded. Glenn Morris restarts play with the free kick.
20:59 Free kick awarded for a foul by Aristote Nsiala on Jack Midson. Sofiene Zaaboub takes the direct free kick.
19:56 Outswinging corner taken from the left by-line by Sofiene Zaaboub.
18:51 Shot from 30 yards by Hamza Bencherif. Blocked by Craig Easton.
18:05 Handball by Luke Prosser. Direct free kick taken by Lewis Chalmers.
17:28 The ball is crossed by Josh Simpson, Jose Veiga makes a save.
15:16 Effort on goal by Josh Simpson from just inside the penalty box goes harmlessly over the target.
15:06 Barry Corr takes the chance to get an effort at goal. Paul Morgan gets a block in.
13:21 Free kick awarded for a foul by Barry Corr on Nathaniel Brown. Lewis Chalmers takes the free kick.
12:19 Corner taken right-footed by Lewis Chalmers, Nathaniel Brown concedes a free kick for a foul on Luke Prosser. Direct free
kick taken by Glenn Morris.
9:29 Shot from inside the six-yard box by Jack Midson goes wide right of the goal.
8:44 Lewis Chalmers takes a outswinging corner from the right by-line to the near post, clearance by Josh Simpson.
7:46 Bilel Mohsni gives away a free kick for an unfair challenge on Hamza Bencherif. The ball is crossed by Anthony Grant, Tyrone
Barnett takes a shot. Glenn Morris makes a save.
6:51 Corner taken by Lewis Chalmers, Tyrone Barnett takes a shot. Anthony Grant gets a block in.
5:17 Effort from outside the penalty box by Anthony Grant goes wide left of the target.
3:45 The ball is crossed by Lewis Chalmers, save by Glenn Morris.
2:21 The ball is swung over by Glenn Morris, Paul Morgan manages to make a clearance.
1:54 Sofiene Zaaboub produces a cross, Aristote Nsiala manages to make a clearance.
0:00 The ref blows the whistle to start the match.
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