Liverpool U21s suffered a 3-2 defeat by Bolton Wanderers on Monday afternoon, despite a spirited first-half comeback by Alex Inglethorpe's team at the Kirkby Academy.
Quick-fire efforts had the away side two goals in front midway through the first half, only for Jordan Rossiter and Jordon Ibe to strike back for a strong U21s line-up, including Martin Kelly and Aly Cissokho.
But as the Barclays U21 Premier League encounter neared a conclusion, Bolton defender Oscar Threlkeld rose highest from a corner to guide a powerful header into the top corner and secure victory.
Ibe threatened to break the deadlock within 45 seconds of kick-off, collecting the ball on the right flank and driving into the penalty area - but his left-footer was blocked out for a corner.
Danny Ward tipped over a whistling punt by Tom Youngs, while in the 13th minute Samed Yesil perhaps should have scored instead of shooting straight at the goalkeeper after capitalising on a defensive error.
But, with a quarter of an hour played, the Reds fell behind; the referee awarded a penalty for a push on Jan Gregus by Jordan Lussey and the Slovakian stepped up to coolly convert past Ward from 12 yards.
The lead was doubled for the visitors following a rapid counter-attack which concluded with Conor Wilkinson directing an effort from inside the area onto the post, allowing Zach Clough to tap home the rebound.
Liverpool reduced their arrears eight minutes before half-time when Rossiter looped a superb header from 15 yards up and over the 'keeper from a pinpoint cross by Cissokho down the left.
And the scores were level before half-time as the Reds converted their own penalty. Ibe was fouled inside the penalty box and took responsibility from the spot, finding the bottom corner with aplomb.
Rossiter was foiled on the goalline when the incisive Ibe delivered into the centre of the Bolton area from his station on the right, as an entertaining opening period drew to a close with the score at 2-2.
When the action resumed, Yesil miskicked at a presentable chance created by the productive Ibe and Youngs dribbled around Tiago Ilori but sent a strike from a narrow angle against the near post.
The second half was far quieter in comparison to the first, but with 10 minutes left on the clock Rossiter sensed a winner when set up by a pass from Ibe - the midfielder's blast was blocked, though.
Instead it was the visitors who cruelly notched the crucial goal. On 84 minutes, an inswinging corner was met brilliantly by defender Threlkeld, who powered a header beyond Ward.
Stephen Sama had an inviting opportunity to rescue a dramatic draw in the final seconds, but the substitute could only direct his near-post header off target in the last genuine action of the match.