Liverpool's difficult start to 2017 continued as Wednesday's 1-0 defeat against Southampton saw Claude Puel's men reach the EFL Cup final, Shane Long the hero in the second leg with his 91st-minute goal.
The Reds had shouts for a late penalty ignored by referee Martin Atkinson after a duel between Jack Stephens and Divock Origi and substitute Long decided the tie just moments later with a cool finish.
Jurgen Klopp's men had won just one of their previous six outings this calendar year - a 1-0 FA Cup win over League Two side Plymouth Argyle - and they knew they were in for a tough task at Anfield following the 1-0 setback from the reverse fixture, a single strike from Nathan Redmond the difference at St. Mary's.
But Liverpool had plenty of reasons for optimism heading into the game following the news earlier in the day that Philippe Coutinho had signed a new long-term deal and the home fans were hopeful the Brazilian could conjure up some magic in the hunt for silverware.
Coutinho was unable to make much of an impact before the break, though, and Liverpool had Loris Karius to thank for still having a chance of making it to Wembley at half-time.
The hosts spurned a number of chances to send the game into extra time after the break before Southampton - who amazingly have not conceded a goal in this season's competition - made sure of their trip to Wembley when Long struck after a quick counter-attack.
Defeat for Klopp was his first in a semi-final as a manager.
1 - Shane Long's last goal v Liverpool was in the FA Cup in 2010 (scored winner in extra time at Anfield for Reading). Momentous.-- OptaJoe (@OptaJoe) January 25, 2017
Southampton, meanwhile, advance and will meet either Manchester United or Hull City in the showpiece on February 26, Jose Mourinho's men defending a 2-0 lead in Thursday's return.
Liverpool got the first half-chance of the game when Adam Lallana did well to win possession deep into Southampton territory before setting up Coutinho, who in turn reached Daniel Sturridge on the edge of the area. The England international quickly turned onto his left foot, only to then aim a tame shot straight at goalkeeper Fraser Forster.
Southampton should perhaps have opened the scoring after a quick break 10 minutes before half-time when Redmond danced past Joel Matip before handing Dusan Tadic a gilt-edged chance from 10 yards out, but goalkeeper Karius came to Liverpool's rescue with a superb save.
Klopp's men made an encouraging start to the second half and nearly drew level on aggregate after a howler from Forster, the Southampton goalkeeper letting Emre Can's powerful shot slip through his hands, only to recover just in time to prevent the ball from crossing the goalline.
Liverpool kept on pushing for the equaliser and Sturridge was next to threaten, inexplicably volleying over the crossbar from close range after Can did well to divert the ball back across goal.
Coutinho came close late on when he curled a shot just wide of the top corner, but it was not meant to be for Liverpool as the Saints edged ahead on the night just moments after Atkinson decided against awarding a spot-kick for after Stephens' challenge on Origi.
Josh Sims set up Long after a rapid counterattack and he beat Karius with a low shot to send Southampton to Wembley, only the second time the club has reached the League Cup final.
Key Opta stats:
- Liverpool have failed to score in all three games v Southampton this season in all competitions.
- Long's last goal v Liverpool was in the FA Cup in 2010 (scored winner in extra time at Anfield for Reading).
- Puel is unbeaten in five previous games against Liverpool as a manager (W2 D3).
- The last time Liverpool failed to score in either leg of a semi-final was in the 1970/71 Fairs Cup v Leeds.
- Liverpool have lost back-to-back home games at Anfield for the first time since October 2012 (all comps).
- This is the first time Klopp has lost a semi-final as a manager, progressing from the previous six.