Liverpool made a shock Carling Cup exit in the third round as League Two's Northampton won the penalty shoot-out.
With the sides locked at 2-2 after extra-time, Abdul Osman kept his cool to slot in the decisive spot-kick.
Milan Jovanovic fired in Liverpool's opener but Billy McKay equalised and Michael Jacobs tapped in to give the Cobblers a worthy lead in extra-time.
David Ngog's late header set up the late drama and as the Reds struggled in the rain, Osman sealed a memorable win.
It was another night of Carling Cup drama for Merseyside football following Everton's surprise exit at Brentford 24 hours before Northampton's visit to Liverpool.
Roy Hodgson opted to give run-outs for a number of fringe players on the back of their weekend defeat by Manchester United, but they started brightly enough as Jovanovic, a summer free transfer from Standard Liege, fired in his first goal for the club after nine minutes.
The Reds were wasteful in front of goal though and would have been wary of their opponents going into the interval with such a slender lead.
And so it proved, as Kevin Thornton out-jumped Sotirios Kyrgiakos to nod over Liam Davis' looping cross for McKay to crash in the equaliser from close range.
With the Anfield faithful sounding increasingly agitated, their team rarely looked capable of grabbing a winner as the visitors held firm at the back to take the match into extra-time.
Northampton, currently 17th in League Two, were the ones dreaming of a fourth-round spot in the Carling Cup as Jacobs poked in after Martin Kelly had blocked Kevin Thornton's shot.
With Kyrgiakos and Kelly both wasteful in the closing stages, it was left for striker Ngog, with four minutes left on the clock, who at last provided the spark to reignite Liverpool's battles.
125:18 Abdul Osman scores a penalty. Liverpool 2-4 Northampton on penalties.
124:30 Penalty missed by Nathan Eccleston.
124:04 Michael Jacobs scores a penalty. Liverpool 2-3 Northampton on penalties.
123:27 Penalty scored by Daniel Agger. Liverpool 2-2 Northampton on penalties.
122:54 Liam Davis scores a penalty. Liverpool 1-2 Northampton on penalties.
122:39 Jonjo Shelvey scores a penalty. Liverpool 1-1 Northampton on penalties.
122:00 Kevin Thornton scores a penalty. Liverpool 0-1 Northampton on penalties.
121:20 Penalty missed by David Ngog.
120:01 The first player steps forward to start the penalty shoot-out.
120:01 Spot kick missed by Steve Guinan.
Extra Time Complete
120:00+1:32 The match is going to penalties.
120:00+0:54 Daniel Agger delivers the ball.
119:03 Sotirios Kyrgiakos fouled by Ben Tozer, the ref awards a free kick. Jonjo Shelvey crosses the ball, Sotirios Kyrgiakos takes
a shot. Liam Davis manages to make a clearance. Outswinging corner taken right-footed by Jonjo Shelvey, Ryan Gilligan makes
117:58 Sotirios Kyrgiakos is ruled offside. Chris Dunn takes the indirect free kick.
115:44 The assist for the goal came from Sotirios Kyrgiakos.
115:44 GOAL - David Ngog:Liverpool 2 - 2 Northampton David Ngog scores a headed goal from inside the six-yard box. Liverpool 2-2 Northampton.
Correction - 114:43 Corner taken by Jonjo Shelvey played to the near post,
114:43 Jonjo Shelvey takes a inswinging corner from the left by-line played to the near post.
113:27 Effort from just outside the area by Jay Spearing goes over the target.
112:33 Martin Kelly produces a right-footed shot from just outside the box that goes wide right of the target.
111:23 Leiva Lucas concedes a free kick for a foul on Nathaniel Wedderburn. Ben Tozer takes the direct free kick.
110:18 Shot from just outside the penalty box by Leiva Lucas misses to the left of the target.
108:04 Sotirios Kyrgiakos gives away a free kick for an unfair challenge on Nathaniel Wedderburn. Ben Tozer takes the direct free
107:16 The ball is delivered by Nathan Eccleston.
106:39 The ball is swung over by Jonjo Shelvey, Ryan Gilligan makes a clearance.
106:19 Jonjo Shelvey takes a short corner.
Extra Time Started
105:01 The match restarts for the second half of extra time.
Extra Time Half Time
105:00+0:26 Substitution (Liverpool) makes a substitution, with Thomas Ince coming on for Daniel Pacheco.
105:00+0:02 A cross is delivered by Jonjo Shelvey, Close range header by Sotirios Kyrgiakos goes wide of the left-hand post.
100:10 Foul by Steve Guinan on Sotirios Kyrgiakos, free kick awarded. Sotirios Kyrgiakos takes the free kick.
99:04 Substitution (Liverpool) makes a substitution, with Jonjo Shelvey coming on for Ryan Babel.
98:00 Courtney Herbert provided the assist for the goal.
98:00 GOAL - Michael Jacobs:Liverpool 1 - 2 Northampton Michael Jacobs gets on the score sheet with a goal from close in to the top right corner of the goal. Liverpool 1-2 Northampton.
92:08 Nathan Eccleston has an effort at goal from outside the area which goes wide right of the goal.
90:25 Nathan Eccleston delivers the ball, clearance made by Liam Davis.
Extra Time Started
90:01 Substitution (Liverpool) makes a substitution, with Nathan Eccleston coming on for Milan Jovanovic.
90:00+3:23 The whistle goes for the end of normal time.
90:00+1:20 Daniel Pacheco has an effort at goal from outside the area which misses left.
89:52 Jay Spearing produces a cross.
89:27 Daniel Pacheco takes the inswinging corner, save made by Chris Dunn.
89:18 Danny Wilson delivers the ball, blocked by Courtney Herbert.
86:37 Free kick crossed by Kevin Thornton, clearance made by Martin Kelly.
86:37 Substitution (Northampton) makes a substitution, with Nathaniel Wedderburn coming on for John Johnson.
86:37 Free kick awarded for an unfair challenge on Liam Davis by Martin Kelly.
Correction - 85:01 The ball is swung over by Daniel Pacheco, Ryan Gilligan makes a clearance.
85:01 The ball is swung over by Daniel Pacheco, Kevin Thornton makes a clearance.
84:30 Corner from the left by-line taken by Daniel Pacheco, Ben Tozer makes a clearance.
83:45 Corner from the right by-line taken by Kevin Thornton, save made by Brad Jones.
83:39 Centre by Courtney Herbert, clearance by Daniel Agger.
82:18 Substitution Steve Guinan on for Billy Mckay.
81:19 Outswinging corner taken by Daniel Pacheco from the right by-line played to the near post, clearance made by Billy Mckay.
80:23 Daniel Pacheco crosses the ball in from the free kick, clearance made by Andrew Holt.
80:23 Booking Liam Davis is given a yellow card.
80:17 Ryan Babel fouled by Liam Davis, the ref awards a free kick.
79:40 Substitution Courtney Herbert is brought on as a substitute for Paul Rodgers.
79:28 Shot from outside the box by Michael Jacobs goes wide right of the target.
75:07 Daniel Pacheco produces a right-footed shot from the edge of the area and misses to the left of the target.
74:20 Kevin Thornton delivers the ball, Daniel Agger makes a clearance.
73:58 Short corner taken by Michael Jacobs from the left by-line.
70:11 Unfair challenge on Leiva Lucas by Abdul Osman results in a free kick. Direct free kick taken by Milan Jovanovic.
69:35 The ball is delivered by David Ngog.
69:08 Ryan Babel fouled by Andrew Holt, the ref awards a free kick. Sotirios Kyrgiakos takes the direct free kick.
67:38 Michael Jacobs crosses the ball, Daniel Agger makes a clearance.
67:32 The ball is sent over by Ryan Gilligan, Sotirios Kyrgiakos makes a clearance.
66:26 Long range effort by Ryan Gilligan goes wide right of the target.
65:21 Free kick taken by Daniel Agger.
65:21 Booking Paul Rodgers booked for unsporting behaviour.
65:12 Milan Jovanovic fouled by Paul Rodgers, the ref awards a free kick.
65:02 Corner taken by Michael Jacobs played to the near post, Milan Jovanovic makes a clearance.
61:31 Kevin Thornton takes a inswinging corner from the right by-line to the near post, clearance by Sotirios Kyrgiakos.
61:08 Short corner worked by Kevin Thornton.
59:59 Strike comes in from Kevin Thornton from the free kick.
59:59 Booking The referee shows Kevin Thornton a yellow card for dissent.
59:29 Jay Spearing handles the ball and concedes a free kick.
59:00 Danny Wilson challenges Paul Rodgers unfairly and gives away a free kick. Kevin Thornton restarts play with the free kick.
57:59 Effort from the edge of the penalty box by Martin Kelly goes wide of the right-hand upright.
55:36 Kevin Thornton provided the assist for the goal.
55:36 GOAL - Billy Mckay:Liverpool 1 - 1 Northampton Billy Mckay finds the net with a goal from close range high into the middle of the goal. Liverpool 1-1 Northampton.
55:08 Corner taken by Kevin Thornton from the right by-line to the near post, clearance by Daniel Pacheco.
52:06 Handball by Andrew Holt. Daniel Pacheco has an effort direct from the free kick.
48:54 The ball is sent over by Ryan Babel, Ben Tozer makes a clearance.
46:39 Martin Kelly delivers the ball, clearance by Ben Tozer.
45:01 The second half begins.
45:00+1:05 It is the end of the first-half.
44:25 Free kick awarded for a foul by David Ngog on Abdul Osman. The free kick is swung in left-footed by Liam Davis, Sotirios Kyrgiakos
manages to make a clearance.
44:08 Free kick awarded for an unfair challenge on Paul Rodgers by Milan Jovanovic. Free kick taken by Ryan Gilligan.
42:56 David Ngog produces a cross, Ben Tozer manages to make a clearance.
42:34 Free kick awarded for a foul by Billy Mckay on Sotirios Kyrgiakos. Martin Kelly takes the direct free kick.
40:03 Liam Davis fouled by Jay Spearing, the ref awards a free kick. Chris Dunn restarts play with the free kick.
39:09 Daniel Pacheco gives away a free kick for an unfair challenge on Liam Davis. Andrew Holt restarts play with the free kick.
37:09 The assistant referee flags for offside against Ryan Babel. Indirect free kick taken by Chris Dunn.
36:31 Ryan Gilligan has an effort at goal from just inside the box that misses to the left of the goal.
35:48 Danny Wilson challenges Paul Rodgers unfairly and gives away a free kick. Free kick crossed left-footed by Kevin Thornton
from right wing, Danny Wilson makes a clearance.
31:08 Effort from long distance by Michael Jacobs goes wide right of the goal.
28:25 Michael Jacobs produces a right-footed shot from outside the penalty box and misses right.
26:44 Kevin Thornton produces a left-footed shot from outside the box and misses left.
26:16 Leiva Lucas takes a shot. Save by Chris Dunn.
25:09 John Johnson sends in a cross, Header from deep inside the penalty area by Michael Jacobs goes harmlessly over the crossbar.
23:44 Unfair challenge on John Johnson by David Ngog results in a free kick. Chris Dunn takes the free kick.
22:01 David Ngog sends in a cross, clearance by John Johnson.
20:53 Ryan Babel is ruled offside. Chris Dunn takes the indirect free kick.
20:18 Leiva Lucas has an effort at goal from outside the area missing to the wide right of the target.
19:05 Unfair challenge on Daniel Pacheco by John Johnson results in a free kick. Free kick crossed right-footed by Daniel Pacheco,
Ryan Gilligan makes a clearance.
18:24 Unfair challenge on Milan Jovanovic by Ryan Gilligan results in a free kick. Free kick taken by Danny Wilson.
17:27 Milan Jovanovic delivers the ball, Liam Davis makes a clearance.
11:24 Liam Davis sends in a cross, comfortable save by Brad Jones.
10:42 Kevin Thornton takes a inswinging corner to the near post, clearance made by Martin Kelly.
8:54 Kevin Thornton takes a shot. Save made by Brad Jones.
8:06 Daniel Agger provided the assist for the goal.
8:06 GOAL - Milan Jovanovic:Liverpool 1 - 0 Northampton Milan Jovanovic scores a goal from inside the six-yard box to the bottom right corner of the goal. Liverpool 1-0 Northampton.
3:42 Martin Kelly gives away a free kick for an unfair challenge on Michael Jacobs. Ryan Gilligan restarts play with the free kick.
2:10 Jay Spearing handles the ball and concedes a free kick. Liam Davis restarts play with the free kick.
2:00 The ball is crossed by David Ngog, clearance made by Andrew Holt.
1:00 Free kick awarded for a foul by Paul Rodgers on Danny Wilson. Direct free kick taken by Danny Wilson.
0:00 The referee gets the game started.
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