After the match finished 2-2, it took 30 punishments before Boro winger Albert Adomah missed to send the Reds through.
Rodgers eased after epic shootout win
Liverpool had led the pack through debutant Jordan Rossiter yet Boro evened out when Adam Reach headed in.
In additional time, Suso bored home for the Reds yet Patrick Bamford's last-minute punishment constrained a shootout.
At that point came the genuine dramatization as the joint most astounding scoring spot-kick challenge in English proficient football unfolded before a scarcely accepting Kop.
Simon Mignolet spared Boro's first punishment from Bamford just for Raheem Sterling to miss Liverpool's fifth and send the shootout to sudden demise.
Amazingly, the following 20 punishments were all scored as player after player from each one side - including both goalkeepers - took care of the weight with aplomb, with a few scoring twice.
Be that as it may when Adomah pushed his kick wide, Liverpool could at last commend triumph.
The 14-13 scoreline matched the result of a Football League Trophy shootout between Dagenham & Redbridge and Leyton Orient in August 2011.
Paying the punishment
The past longest League Cup punishment shootout was 9-8 on three events - Arsenal v Rotherham in 2004 and Man City beating Stoke and Aston Villa beating Colchester both in 1982
The longest in the FA Cup was Macclesfield beating Forest Green 11-10 in November 2001 in the first round
The record for the best sequential breaks in English football is 29 when Brockenhurst beat Andover 15-14 in the Hampshire Senior Cup a year ago
The result will alleviate Liverpool supervisor Brendan Rodgers, whose side have lost three of their initial five class matches and face Everton in the Merseyside derby on Saturday.
Boro, interestingly, will be crushed to have verged on recording their first win at Anfield since 1976 after more than matching the Reds in excess of 120 minutes of a throbbing container tie.
With commander Steven Gerrard rested, 17-year-old institute item Rossiter was given his presentation at the base of the Reds midfield, and he just took 10 minutes to make his imprint.
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Brockenhurst FC v Andover Town FC
Brockenhurst and Andover score record-breaking 29 sequential punishments
After a long ball brought on bedlam in the Boro safeguard, debutant goalkeeper Jamal Blackman spared forcefully from Rickie Lambert. At the same time the ball fell sympathetic to Rossiter, who cleared a low shot past Blackman's thrashing legs before wheeling endlessly in joy.
Boro scored a merited equalizer on the hour after Mamadou Sakho was punished for taking care of a cross.
Award Leadbitter's free-kick from the right flank escaped the Liverpool safeguard and welcomed Reach to apply the headed completion from inside the six-yard box.
Live content
Take after the show as it happened in our live content discourse.
Rodgers presented Mario Balotelli for the ineffectual Lambert, yet at the same time Boro debilitated.
Also with five minutes staying, Lee Tomlin's sublime opposite pass sent Clayton clear, yet his strike cannoned off Mignolet's close post.
In additional time, Blackman spared long-go strikes from Jose Enrique and Sterling before substitute Suso put the Reds in front with his first Liverpool objective.
Ex-Liverpool shield Jamie Carragher on Jordan Rossiter
"Not celebrated as energetically since Dudek spared that pen! Totally enchanted for @jordan_rossiter and his family & companions viewing."
Adam Lallana and Enrique connected up well down the left and when Balotelli's exertion was just half cleared, the Spanish forward picked his spot from 12 yards.
Be that as it may there was still time for an alternate contort as Boro were honored a punishment in the most recent moment of additional time.
In the wake of Sterling had doled the ball out, Kolo Toure fouled Bamford, and the Boro substitute ventures up to beat Mignolet and take the attach to extra shots.
How BBC Radio 5 live analyst Conor Mcnamara portrayed the finale
"The standard of punishments has been phenomenal! Someone some place will be working out what the record is for the most punishments in a shootout as here come Middlesbrough again - and its wide! Albert Adomah has put wide and that closures a punishment shootout that experienced 15 kicks each! Liverpool celebrate as Albert Adomah is quickly comforted by his buddies. Such show at Anfield, such splendid, splendid punishments to watch from both groups. Middlesbrough go home baffled. Unfathomable! Splendid to be here for that."
Middlesbrough administrator Aitor Karanka:
"These are the sort of amusements where you must be extremely glad for your players, your gathering, your club, everything.
"I think we have indicated everyone what sort of club Middlesbrough are. I don't have numerous words to clarify my emotions at this moment.
"We have played against a Champions League group at Anfield and you know how troublesome this is for us - and we have played eye to eye against them.
"Despite the fact that we have lost, our players ought to appreciate this."
Albert Adomah misses
Adomah's miss brought a 19-moment shootout to an end
Liverpool have won the League Cup a record eight times
Liverpool have won the League Cup a record eight times
Suso celebrates with buddies
Suso's objective in additional time was his first for Liverpool
Jordan Rossiter
Jordan Rossiter has been compared to chief Steven Gerrard
Adam Reach
Adam Reach scored a merited equalizer for Middlesbrough
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