Even for a club renowned for heart-stopping drama in cup ties, this was new territory.

Liverpool FC advanced to the fourth round of the Capital One Cup but only after the most extraordinary penalty shootout in the club's 122-year history.

No fewer than 30 spot-kicks were required before Brendan Rodgers ' players raced to embrace Simon Mignolet and relief engulfed Anfield with Middlesbrough defeated.

The Reds' ambitious plans off the field to redevelop their historic stadium may have been given unanimous approval by the city council, but securing progress on the field is proving more problematic.

Teenage debutant Jordan Rossiter fired them in front early on but the Championship outfit hit back and deservedly equalised through Adam Reach.

Liverpool substitute Suso appeared to have settled the tie in the second period of extra time but this team's habit of causing problems for themselves reared its ugly head once again.

In the dying seconds Raheem Sterling's slack backpass led to Kolo Toure upending Patrick Bamford, who slammed the resulting penalty past Mignolet.Liverpool also drew first blood in the shootout as Mario Balotelli scored and Bamford was denied.

Lucas Leiva, Adam Clayton, Adam Lallana, Adam Reach, Suso, Albert Adomah all converted, giving Sterling the opportunity to win it but his effort was weak.

Substitute Jelle Vossen sent it to sudden death and both sides refused to caved in.

Debutant Jordan Williams, George Friend, Kolo Toure, Daniel Ayala, Mamadou Sakho, Ryan Fredericks, Javier Manquillo, Kenneth Omeruo, Jose Enrique and Yanic Wildschut all netted, leaving the keepers to do battle at 9-9.

Mignolet and Jamal Blackman beat each other and it was back to the start again.

Balotelli, Bamford, Lucas, Clayton, Lallana, Reach and Suso scored but Boro finally blinked with Adomah blazing wide.

It was an epic ending to a night.

Rodgers made seven changes following the weekend setback at Upton Park with Mignolet, Manquillo, Lucas and Sterling the only players retained.

Steven Gerrard and Dejan Lovren were among those given the night off ahead of Saturday's Merseyside derby but there were sufficient quality on show to avoid such a struggle.

There was an early scare when former Reds defender Ayala rose to meet Grant Leadbitter's corner but Mignolet kept it out.

Liverpool soon settled with Sterling leading the charge from a central role behind Rickie Lambert in Rodgers' 4-2-3-1 formation.

It was the presence of the teenager which helped spark the panic that led to Rossiter's opener inside 10 minutes.

As Sterling pursued Lucas' through ball, Blackman and Omeruo - both on loan from Chelsea - made a mess of clearing their lines.

Lambert pounced but his strike was blocked by Blackman. The rebound dropped to Rossiter 30 yards out and he drilled it hard and low past the debutant shot-stopper and into the net.Anfield erupted as the 17-year-old from Everton Valley set off on a celebratory dash towards the Main Stand, the youngster leaping into the air with joy etched across his face.

It was the sixth fastest goal by a Liverpool player making his debut post-War - beating the likes of Luis Suarez and Fernando Torres.

Rossiter continued to impress as he snapped into tackles and used the ball intelligently.

The fact he felt so at ease at this level was underlined by the sight of him barking orders to Toure, a two-time Premier League title winner who was playing top-flight football in England when Rossiter was five years old.

Liverpool dominated possession with Enrique and Lallana linking up well down the left, but they failed to turn it into clear cut chances.

The longer the first half went on the more Boro's grew in stature.

Kike saw his volley deflected over the bar off Lambert and then the Spanish striker was thwarted when Mignolet reacted smartly to save bravely at his feet.

Rodgers' decision to play the Belgian, rather than hand an opportunity to deputy Brad Jones, was surely based on a desire to help restore some confidence after the struggles of recent weeks.

Mignolet was called into action again eight minutes before the interval when he beat away Lee Tomlin's fierce strike.

Rather than nipping the Boro revival in the bud, Liverpool allowed it to blossom with a sloppy start to the second half.

Just 11 seconds had elapsed when Tomlin was allowed to charge forward unchallenged from halfway and flash a 25-yarder narrowly wide.

The warning wasn't heeded and the equaliser arrived in the 62nd minute in painfully familiar circumstances.

Sakho was booked for handling Adomah's cross and yet again a set-piece proved Liverpool's undoing. Leadbitter whipped it into the six-yard box and Reach got ahead of Enrique to nod home from close range.

Liverpool struggled to muster a response and the Kop roared its appreciation when Rodgers summoned Mario Balotelli from the bench. The Italian replaced Lambert, who passed the armband to Kolo Toure having endured a frustrating night on his first start.

Worryingly, Middlesbrough looked the more likely to find a winner in normal time.

Mignolet clawed away Adam Clayton's shot and Toure slid in to prevent Tomlin from converting the rebound.

Rodgers handed out a second Reds debut late on as 18-year-old Wales youth international Williams came on for Rossiter.

Boro were inches away from glory when Clayton hammered against the angle of post and bar, while at the other end Ayala somehow got away with handling Sterling's cross.

It was a similar story in extra-time with Liverpool creating their own problems by giving away a string of needless free-kicks.

When they did work the ball into decent areas Lazar Markovic's infuriating reluctance to shoot meant Blackman went untested. It was no surprise when the Serbian made way for Suso.

In the second period both Enrique and Sterling forced sprawling saves from Blackman before the Reds went in front in the 109th minute.Enrique exchanged passes with Lallana and his cross sparked chaos in the box. The loose ball fell to Suso, who clinically tucked away his first goal for the club.

Liverpool were seconds away from victory when they pressed the self-destruct button.

Sterling's backpass was pounced on by Ayala, who sent Bamford racing clear. Toure brought him down and the substitute picked himself up to score from the spot.

Somehow the night enjoyed a happy ending.

Man of the match: Jordan Rossiter. The teenager could hold his head high after shining on his debut.

Source: Liverpool Echo