Liverpool was knocked out of the second cup competition in a week Saturday as Championship side Wolves won 2-1 at Anfield.
It continued a miserable run of form this January that has seen Jurgen Klopp’s side win just one game in eight.
Worse, they have exited both the League Cup and FA Cup competitions which the side would have targeted as potential trophies to add to the club’s cabinet this year.
Their last win came on December 31, beating Manchester City 1-0.
That result took them within six points of Premier League leaders Chelsea, ending a superb 2016.
But, one month later, they sit ten points off of Chelsea and have slipped from second to fourth with their hopes of Champions League qualification under threat.
Their slump has coincided with star man Sadio Mane’s absence at the African Cup of Nations and has included two defeats to Southampton in the League Cup semi-final and a loss to Swansea in the league to add to this latest humbling by Wolves.
There have also been draws with Sunderland, Plymouth and Manchester United, with their only victory coming in the FA Cup third round replay at League Two side Plymouth.
It could ultimately prove a decisive period for all the wrong reasons for Liverpool who are in desperate need of turning things around next month.