Liverpool suffered defeat for only the second time this season after going down 1-0 to Tottenham Hotspur in the Carabao Cup semi-final first-leg on Wednesday evening.
Starts for Conor Bradley and Diogo Jota headlined the Reds' line-up, with Trent Alexander-Arnold and Luis Diaz dropping to the bench, as Spurs started new signing Antonin Kinsky in goal.
There were promising signs earlier on for the host who could've gone ahead on eight minutes through a side-foot effort by Radu Dragusin but Alisson Becker dived to repel him.
At the same time, a lengthy stoppage had the attention of the home team go to the bench to introduce Brennan Johnson ahead of injured Rodrigo Bentancur.
Nothing serious took place though as the match resumed with the Reds on the charge and coming close through a free header in the box by Alexis Mac Allister.
Prior to that, Liverpool also needed to make a first half substitution as Japan international Wataru Endo came on for Jarell Quansah who couldn't carry on playing.
The urgency didn't drop as the second period got underway, with the visitors shaving the far post through a sharp curler by Mohamed Salah.
Liverpool were soon in danger when a poor pass by Alisson led the host in unfortunately though Pedro Porro failed to capitalise and fluffed his lines.
At the other end, Spurs were on the back-foot when a ball in-behind released substitute Darwin Nunez for a near post finish but Kinsky narrowed him down
Alexander-Arnold who had also come off the bench looked to bounce back after days of criticism through a low attempt across the face of goal, but Dragusin cleared from the goal-line.
Spurs seem to have gone ahead when Dominik Solanke finished from close-range having raced clear, but it was called back for offside by the Video Assistant Refereeing team.
Although, the winning goal arrived four minutes from time as Lucas Bergvall ran in the box and combined with Solanke to calmly pick out the near corner, although the visitors felt the former should have been sent off minutes earlier.
Liverpool almost snatched a draw in added time through Nunez's first-time strike at the near post, but Kinsky palmed for a corner as Spurs held on for the first-leg win.