Liverpool were beaten 1-0 by Tottenham Hotspur on Wednesday night in the opening leg of their Carabao Cup semi-final tie.
A solitary strike from Lucas Bergvall four minutes from the end of normal time settled the affair at Tottenham Hotspur Stadium, leaving the hosts holding a slender advantage ahead of the Anfield return on February 6.
Team news
Liverpool made four changes for the contest, with Conor Bradley, Kostas Tsimikas and Jarell Quansah stepping into defence.
In attack, meanwhile, Diogo Jota returned to lead the Reds’ frontline in the capital for his first start since October.
First half
It was the hosts who started the better of the two teams, pressing Liverpool high and forcing several stray passes in the final third.
The early threat resulted in the opening chance of the game, with Alisson Becker reacting well down low to his right to keep out a Radu Dragusin effort, the defender turning a Heung-Min Son shot towards goal inside the box.
Following the passage of play, there was a lengthy stoppage as Rodrigo Bentancur was stretchered from the field, being replaced by Brennan Johnson.
Son again threatened the Liverpool defence a short while later, stepping outside of Bradley on the left to drill a low ball into the six-yard box, though teammate Dominic Solanke could only turn wide.
Liverpool returned fire at the other end, seeing a Mohamed Salah effort flash past the post from distance, before they were forced into a change of their own, Quansah picking up a knock with Wataru Endo the replacement.
Alexis Mac Allister then saw a header saved from close range following a dead ball delivery from Tsimikas, the ball finding his free run into the box.
Ahead of the interval, Liverpool threatened once more at a swift break via Cody Gakpo, with the forward unleashed a fizzing drive at goal that nearly caught goalkeeper Antonin Kinsky by surprise to close out the opening 45.
Second half
The game restarted at pace after the change of ends, both teams searching for the opening goal with a number of crosses into the area.
Neither goalkeeper, however, were being properly tested as the two sides battled for possession.
Tottenham spurned a good chance to break the deadlock, capitalising on Bergvall stealing the ball from Alisson on the edge of the area.
Pedro Porro first saw his resulting shot blocked by Virgil Van Dijk, ahead of the ball finding its way back into his path on the right, though he could only lift another effort past the far post with a dink.
On the hour, the Reds opted to make a triple change, Darwin Nunez, Trent Alexander-Arnold and Luis Diaz replacing Jota, Bradley and Gakpo respectively.
Nunez almost made an immediate impact following his introduction, guiding a header at goal from 12 yards out after a looping Mac Allister cross, but the chance was well caught by Kinsky in the Spurs net.
The No.9 again broke free in the box, latching onto a Salah ball forward, though his strike was saved by the onrushing home stopper once more.
Alexander-Arnold then came within inches of finding the lead for the Reds, hitting a stunning low drive at goal from a tight angle with his right boot, only for the retreating Dragusin to clear off the line, ahead of Mac Allister's follow-up falling the wrong side of the post.
In minute 76, Tottenham had the ball in the back of the net via Solanke's break, the striker darting onto a ball over the top to finish past Alisson.
The goal, though, was ruled out by VAR after the forward strayed offside in the build-up with the score remaining level.
Spurs, however, weren't to be denied four minutes from time, as Bergvall struck a lot shot into the bottom corner of the net, meeting Solanke's cut-back to finish well.
Nunez almost levelled in added time with a clever reaction volley from a Diaz cross, though Kinsky pushed his effort wide to see out the match.
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