Despite a late headed goal from Mohamed Salah, they were unable to complete the comeback, losing 2-1 to a Manchester United side that jumped above Liverpool in the Premier League table despite their poor start to the season.
The defeat leaves Klopp with more questions than answers with his side struggling to create chances up front, but more worryingly, looking porous at the back. He admitted after the game that his side are giving him a headache, pinning some of the problems on a depleted senior squad.
He explained: “We are in a tricky situation injury wise. We got through the week with 14, 15 senior players available and now have to make sure they don't get injured.
"We should have won this game. I know it sounds ridiculous but that is how I saw it.”
Next up, Liverpool face newly-promoted Bournemouth, who lost 3-0 to Arsenal on Friday night.
"I am concerned about our situation, but that is how it is. We prepare for Bournemouth (on Saturday) and Newcastle (next Wednesday) now." he added.
"It was not a perfect performance, it was clear United would get out of the blocks but we were not 100% ready.
"We had to keep chasing the game and that is not what you want to do. It makes it difficult with their counter-attacking threat. The second goal is hard to take, it was offside, but we have to work with it," added the German.
Check out all the statistics from Monday night’s game with Flashscore.