It all looked to be going to plan for Liverpool, as keeping Villarreal at 0-0 and bringing them back to Anfield would have been seen as a positive with the home support behind the reds, but they were undone right at the death.
Despite Simon Mignolet pulling off a nice save to keep the scores at 0-0 minutes before Adrian Lopez pounced late on after a square ball from Denis Suarez.
But really it was all about the ball from Bruno that took Kolo Toure completely out of the picture.
The tie is by no means over, but that's a blow for Jurgen Klopp's men.
The German manager explained before the game that he had left Daniel Sturridge out as he wanted to utlise a 4-3-3 which did not suit the Englishman, but that decision will surely be called into question now.
All eyes will be on Anfield next week as the Reds will look to pull off another European comeback.
