Bobby Adekanye left the field on a stretcher as Liverpool under-23s slumped to a Premier League 2 defeat at Arsenal.
Adekanye was treated for several minutes and received oxygen after injuring his right knee towards the end of a chastening 4-0 defeat for Neil Critchley's side.
With Lazar Markovic in their starting line-up, the young Reds were no match for the reigning champions – helmed by former Arsenal star Freddie Ljungberg – at Boreham Wood's Meadow Park on Friday night.
Despite dominating for significant periods, Liverpool were undone by two goals in three minutes midway through the first half.
Liverpool vs Southampton
The first came from a breakaway on 22 minutes, which was finished expertly by Bukayo Saka with a shot across Reds goalkeeper Kamil Grabara into to the bottom corner.
The second goal, though, was a horror show for the visitors, as Arsenal pounced on hesitant passing across the back from Nat Phillips and George Johnston allowed England under-21 international Eddie Nketiah to score.
Liverpool created chances during an improved second-half showing but the Premier League 2 champions extended their advantage on 79 minutes through Joe Willock.
Adekanye's injury seven minutes from time was a sad postscript to an evening to forget for the young Reds, with Nketiah adding another goal in injury time.
Markovic fails to make impact
The inclusion of Markovic provided the pre-match intrigue, not least when it became clear the Serbian would be operating as the central striker.
Having seen a move to Anderlecht fall through on transfer deadline day last month, the 24-year-old has been left in limbo after failing to make the cut for Liverpool's Premier League and Champions League squads.
Indeed, Markovic has been banished to train with the U23s, with this his first appearance for Critchley's side this campaign.
It was something of a mixed bag. There was understandable rustiness during the first half, not least when failing to back himself when sent clear one-on-one.
Markovic, though, warmed to his task, and despite an understated evening still had three decent chances to score.
He glanced a header wide from an Adam Lewis free-kick, and forced two second-half saves from Arsenal goalkeeper Deyan Iliev, the second of which should have been converted after being found unmarked at the far post by another fine Lewis delivery.
Markovic was replaced with 12 minutes remaining. Until January, at least, regular U23 football will be the limit of his ambitions.
Tough evening for youngsters
The quality of Arsenal's attacking play meant it was a difficult evening for many of Liverpool's youngsters.
Often, though, the Reds' problems were of their own making, not least the second goal.
Rafa Camacho, who started at right-back before switching to wing-back as Liverpool changed formation at the break, will have learned much from a tough test up against the pace, power and trickery of Saka.
But he wasn't alone in struggling as Arsenal underlined their strength in depth. They were last year's champions for a reason.
Lewis, though, impressed down the left for the Reds, his deliveries from out wide offering Liverpool's most likely route back into the game.
And Adekanye was Liverpool's biggest threat, dragging one effort wide, having a shot cleared off the line and later within inches of forcing the ball home.
However, his night ended in worrying fashion when, after a seemingly innocuous passage of play, he fell to the turf clutching his right knee before eventually departing on a stretcher.
Having only last week trained with the first team and played a part in the UEFA Youth League win over Paris Saint-Germain in midweek, any serious injury would be an untimely blow for 19-year-old Adekanye.
Liverpool weren't helped by some questionable officiating – quite how Tolaji Bola wasn't sent off for taking out Adekanye only the referee will know – but were very much second best on the night.
LIVERPOOL UNDER-23s (4-3-3): Grabara; Camacho, Phillips, Johnston, Lewis; Chrivella, Virtue, Christie-Davies (Coyle 74); Adekanye, Markovic (McAuley 78), Millar (Gallacher 46). Subs: McKenzie-Lyle, Tagseth.
