Swansea City qualified for the League Cup semi-finals by the narrowest of margins this evening, progressing thanks to a Seb Hines own goal 10 minutes from time.
Middlesbrough have played 12 successive ties away from home in this competition and dealt with a Swans side featuring Michu, Nathan Dyer and Leon Britton for long spells.
Both sides have enjoyed strong starts to their league campaigns and were looking to make the final four of a competition blown wide open by Arsenal's shock defeat to Bradford City last night.
Here, Sports Mole analyses a historic victory for Michael Laudrup's side.
Match Statistics
Swansea City
Shots 8
On Target 7
Possession 62%
Corners 9
Fouls 6
Middlesbrough
Shots 10
On Target 6
Possession 38
Corners 4
Fouls 11
Was the result fair?
No. The visitors shaded a drab first half and looked threatening on the break throughout. Swansea dominated possession in the closing stages and eventually forced the vital mistake but Tony Mowbray has every right to feel aggrieved with the full-time score.
Swansea City's performance
Under-par, by the high standards set in the first few months of Laudrup's tenure. Nathan Dyer and Wayne Routledge struggled to feed Michu and a normally fluid midfield was regularly disrupted by a resolute Boro display.
Middlesbrough's performance
Encouraging. The Championship high-flyers had their moments and if Grant Leadbitter were more clinical extra time would have been the least Boro got for a battling performance.
Sports Mole's man of the match
George Friend: A marauding performance from the left-back will have caught the eye of Premier League scouts across the country. Friend showed pace, drive and endeavour for much of the 90 minutes and provided Boro with an outlet during spells under pressure.
Biggest gaffe
No prizes for correct answers here. Seb Hines flicking the ball into his own net less than 10 minutes from time to undo a match filled with important interceptions from the young defender.
Referee's performance
Lee Probert decided not to award Swansea a strong penalty shout after Hines had gone to ground to stop Ki in the area. Nicky Bailey was also harshly penalised for a late lunge which led to Jonathan De Guzman hitting the bar with a free kick from close range.
What's next?
Swansea: Laudrup's side travel to White Hart Lane on Sunday to face a Tottenham Hotspur side still smarting from last weekend's late defeat to Everton.
Middlesbrough: Mowbray's men return to their Championship promotion push this weekend with a home match against Wolverhampton Wanderers.
