Liverpool's disappointing January saw them exit the League Cup at the semi final stage ending one of the two possible routes to Wembley.
And with Liverpool's form this month being so disappointing - there is no guarantee that they can get past Wolves in just over 48 hours time - especially with players likely to be rested for the visit of Chelsea just another three days later.
Klopp recalled Daniel Sturridge to the starting line up - but just as at Southampton a fortnight ago the England man couldn't finish his opportunities. He blazed one shot over from 6 yards out when the easier option would have been a controlled dink into the net.
Claude Puel, the Southampton boss, has enjoyed two 1-0 victories over the reds in recent weeks and Southampton continue their resurgence after a difficult period with wantaway players. For the reds it was the first time we have lost both legs of a League Cup semi-final.
Liverpool welcomed back Joel Matip and the injury time goal from Shane Long was no slight on his performance - the goal coming in the dying embers of a game that Liverpool were trying to send to extra time.
But the reds were misfiring and a standard pattern is emerging. When Sturridge plays, and Firmino is pushed out of centre, the reds score less goals. Not to mention the huge impact that Sadio Mane at the African Nations appears to be having on the team.
The reds dominated possession as the Saints put up another defensive display that Liverpool have yet to figure out how to deal with.
Liverpool were unlucky not to be awarded a penalty for a Shane Long handball but over the course of two legs there can't be too many complaints about the overall result.
Before the game the Liverpool crowd had welcomed the teams with flares outside the ground but there was little spark inside Anfield tonight from either the players or the fans and the next two games, if they go badly, could effectively end Liverpool's hopes of silverware this season.