Liverpool's hopes of picking up a trophy for the second consecutive season suffered a huge blow with a 2-0 defeat at Zenit St Petersburg, which leaves their Europa League chances hanging by a thread.
The Reds paid for missing several chances in Russia, as Luis Suarez in particular was guilty of missing presentable openings which could have secured them an away goal.
Brendan Rodgers was then left frustrated as a stunning goal from Hulk and a Sergei Semak strike soon afterwards gave the hosts a 2-0 lead to take to Anfield, where the Reds will now have to stage a stirring comeback to earn a spot in the last 16.
Here are Liverpool's player ratings from a difficult night in Russia:
Who knows how Liverpool's night would have gone had Reina not made a terrific early save to thwart their Russian opponents?
So often in recent weeks, months and even years the Spaniard has been pointed to as a weak link in the Reds' rearguard, but although this was another defeat the goalkeeper couldn't be faulted.
He can only hope to build on this display.
A typically lung-bursting Johnson run produced just one of many chances that Liverpool had on another evening of frustration.
However he was nowhere to be seen when Sergei Semak doubled Zenit's lead so soon after Hulk's opener, and the full-back will be left as disappointed as anyone by Liverpool's late lapses.
Earlier in the season it seemed that Carragher's only hope of making an appearance lay in the Europa League, but now he's picked for every game.
He did well to deal with Zenit's early onslaught, but like the rest of the team he struggled the longer the match went on, with an element of tiredness perhaps creeping in to the old bones.
This was a return to Zenit for their former Slovakian defender, and for the most part Skrtel will have enjoyed his return to a former home.
The dominance he once used to display in his defending has now been lacking for some time though, and the centre-back will have been frustrated to see two late goals undo the hard work he and his team put in.
Getting Enrique back to the full fitness and sharpness he showed at the beginning of the season should be a key hope for Liverpool, and at least the Spaniard got another 90 minutes under his belt here.
Like the rest of his teammates his defending was found wanting in the closing stages. But he did show some promise going forward, even if it was more limited than would be ideal.
It was a return to action for the Welshman, who performed admirably in an area of the field that Zenit had set out to dominate.
Allen has been the main loser of Jordan Henderson's fine recent form, but alongside him here he looked neat and tidy, although lacking in attacking verve once more.
It was possibly a game too far for the midfielder, whose all-action pressing game is effective in the Premier League but not here.
Henderson saw a lot of the game pass him by and looked tired in patches, particularly when he was shrugged off the ball far too easily in the build-up to Hulk's fine goal.
One day Liverpool will have to be able to rest Gerrard without fearing the worst, but that day doesn't look like it's coming any time soon.
Following on from his morale-sapping penalty miss on Monday night, Gerrard took to the field again looking a weary figure. Although he once again got through the game he never managed to hit fifth gear.
He'll need to rest up ahead of Swansea now.
From outcast to seemingly undroppable, Downing played again here as Rodgers continues to try and get the best out of a man he once ignored.
He didn't do anything special, and would perhaps benefit from a rest in the weeks to come.
It was a welcome return to the starting XI for the youngster, who can add another experience to his burgeoning career.
Sterling was lively in the first half, and almost provided a goal for Suarez when his pull back was flicked wide by the Uruguayan.
Like his team's, his threat did recede somewhat after that, but he could have done enough to pick up a start at the weekend.
It is difficult to evaluate Suarez's performance. Had he taken his chances then Liverpool would arguably be already through to the next round. But he missed them, and now they face probable elimination.
Still, without him the Reds would have been utterly toothless, and so he has to be given credit for his sheet quality on a rare off-night.
He'll have better ones. Liverpool will hope he has one next Thursday.