It was supposed to be a night where Liverpool could stop the rot, but close to 50 shots didn't manage to lift the gloom around Anfield and Brendan Rodgers as they were taken all the way to penalties by League Two outfit Carlisle United.
When Danny Ings opened the scoring it looked as if the Reds could be on for a pretty productive night, but they were soon pegged back by Derek Asamoah. The failure to break down the visitors from then on prompted boos from the Anfield crowd at every interval, as Liverpool tried pot shot after pot shot in an effort to breach stubborn opposition.
There is an almighty sense of relief that they managed to make it to the next round of the competition against Bournemouth, but they wouldn't have wanted extra time to make it through ahead of this weekend's Premier League clash with Aston Villa, especially given the amount of players that are likely to start against Villa.
Here are five things learned from the side's poor display against Carlisle:
Adam Bogdan had his uses... though counting may not be his strong point
It was a decent penalty shootout performance from the Liverpool debutant, who managed to save three of the spot-kicks he faced, with a couple of them impressive - though question marks need to be asked about Carlisle's equaliser. After he saved the penalty that resulted in Liverpool's progression into the next round, he didn't realise it had won the tie for the home side. It wasn't really a night for celebration, even if the Reds did make it through.
No midfield combination seems to work and Milner could be a problem in the middle
Liverpool's central midfield looked exposed against last night and you only have to look at the Carlisle equaliser to see how soft the middle of the park is for Liverpool at the moment. Joe Allen was making his first appearance of the season, and was clearly lacking a bit of fitness, while for the second consecutive game, Milner looked increasingly exposed in the middle and someone needs to be doing the leg work in the middle of the park in order for it to be effective.
Liverpool's tactics seem to be try the same thing again and again and hope for a different result
It was a bit like watching a recording on repeat throughout the game. Liverpool would work their way to the edge of the penalty area, have a shot and not score. Even with a system that accommodates natural width, they somehow managed to make things difficult for themselves by getting the wing-backs to tuck in in the final third. It made no sense as they continued to toil.
Danny Ings - the main reason to be positive
At least they have a striker that is in some sort of form, and seems to be one player the fans have taken to during this terrible run - as his work ethic, desire, and willingness to run is there for all to see. There is also the bit of quality, and he's starting to take up the right positions, as well as managing to score two in two. So if there's one positive for Liverpool to hang their hats on, it's Danny Ings.
It's hard to see where the next win is coming from
This probably isn't something learned. It's just a statement of fact. There were a couple of signs of life during Sunday's draw with Norwich City in the Premier League and Liverpool should have gone on to win the game, but this was reverting to type. They can't score two goals in a game, and when they score one they feel the need to concede, and it's now a painful ordeal for Liverpool fans.