Real Madrid's Champions League fate is out of their hands after Zinedine Zidane's side succumbed to a 2-0 loss to Shakhthar Donetsk in Ukraine.
Real dominated the first half but were ultimately unable to make the breakthrough, with Anatoliy Trubin denying Karim Benzema before sticking out a palm to parry a Marco Asensio shot that looked like it was destined for the back of the net.
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Asensio was arguably the most threatening of the visitors' front line and had beaten Trubin from point-blank range early on, only to see his effort clip the woodwork and go wide.
Shakhtar offered precious little in the first half but came to life after the break. Taison forced a good stop from Thibaut Courtois, but the visitors were then undone by a counter-attack.
Marlos brought the ball forward and fed Matvyenko, whose pass towards the forwards was partially intercepted by Ferland Mendy. Both Mendy and Raphael Varane waited for the other to clear the ball and Dentinho nipped in to fire his side ahead.
The visitors continued to dominate possession but did precious little with it. With minutes left, they were cut open on the break once more, with Manor Solomon dribbling from inside his own half to the Madrid box unchallenged before firing one past Courtois.
The victory sees Shakhtar move up to second in Group B on seven points, level with Real but ahead on their head-to-head record, while Borussia Monchengladbach lead the group with eight points and could qualify with a win over Inter Milan later on Tuesday.
What on earth has happeneed to Real Madrid? This was a performance emblematic of Real Madrid's season so far. They looked sharp in the first half but were way, way off the boil in the second. Their defence was rudderless and clumsy and their attacking play lacked purpose and was ponderous. Somehow the Spanish champions are facing the unthinkable - elimination from the Champions League group stage, which has never happened before in their history.
Gone are the days of summer, when Real Madrid produced an extraordinary run to the Liga title. Zinedine Zidane has largely been a man with a golden touch at the Bernabeu but there will be serious questions asked of his future if his side fail to make the last 16, with their domestic form also inconsistent and stuttering.
MAN OF THE MATCH
Anatoliy Trubin (Shakhtar): Shakhtar Donetsk did not look like a team capable of winning this match for the first 45 minutes, not least when their main goalscoring threat Junior Moraes was injured in the early stages. The hosts had their teenage goalkeeper to thank for their win as he made a good save to deny Benzema and an even better one to prevent Marco Asensio from scoring. Most of the visitors' efforts were straight at home in the second half but he still had to make those saves and his judgement on crosses belied his young years.
Shakhtar: Trubin 8, Dodo 7, Bondar 6, Vitao 6, Matvyenko 6, Marlos 7, Kovalenko 7, Tete 7, Taison 8, Moraes N/A. Subs: Dentinho 8, Soloman 8, Maycon 6, Fernando N/A
Real Madrid: Courtois 6, Vazquez 6, Varane 5, Nacho 5, Mendy 5, Kroos 5, Modric 6, Rodrygo 6, Odegaard 6, Asensio 7, Benzema 6. Subs: Vinicius Junior 6, Isco 6, Mariano 6
5' POST! Benzema with some quick feet on the edge of the box squares it to Asensio, whose short range clip beats Trubin but comes off the woodwork and behind for a corner. He should have scored.
11' SAVE! Vazquez and Modric combine well and the Croat releases Benzema, who shoots early, but Trubin beats it away.
30' SAVE! Trubin has certainly been the busier goalkeeper. Asensio is on the end of some fine build-up play and shoots with venom but Trubin sticks out a hand to palm it wide. You feel like it's only a matter of time until Madrid get their goal now.
53' SAVE! Shakhtar are attacking with much more intent. Taison's quick feet beat Varane and Courtois has to get down well to save his powerful, low shot. The Belgian keeper has hardly had anything to do so far.
57' GOAL!!!! Shakhtar lead! The hosts counter well with Marlos, who feeds Kovalenko. Mendy makes the interception but neither he nor Varane follow it up and Dentinho is there to capitalise. We have an interesting game on our hands now...
67' SO CLOSE TO 2-0! Tete's pull back finds Kovalenko on the penalty spot but Varane flies across to make the block and deny to the hosts a second goal. That could have been curtains...
82' GOALL!!!!!!!!!!!!!!!!!!!!!!!!!! This is game over now and Real Madrid are heading to defeat. Soloman picks up the ball as Shakhtar break and runs a full 60 yards unchallenged, cuts onto his right foot and rifles the ball into the bottom corner.