Real Madrid suffered a second home defeat in five days as they slumped to a shock loss against Champions League opponents ravaged by players ruled out by positive coronavirus tests, conceding three times in 14 first-half minutes.
The 13-time European champions were heavy pre-match favorites against the Ukrainian side, whose coach, Luis Castro, had described his squad's preparations as a "nightmare".
Castro was without several key players after Covid-19 ripped through his squad, including star striker Junior Moraes, but his patched-up side raced into a 3-0 half time lead at the Alfredo Di Stefano.
"It's a bad moment," said Madrid coach Zinedine Zidane, speaking after a post-interval comeback from his side resulted in a painful 3-2 defeat.
"At least we showed fight in the second half. The players are annoyed: they're champions, so it's natural. It's my job to find solutions because these kind of games can't happen."
Having lost 1-0 at home to Cadiz in La Liga on Saturday, Madrid might have been thankful that no fans were at their training ground to watch a stunning opening 45 minutes in which they conceded three times during the opening period for the first time since Lyon visited in September 2005.
Tete struck in the 29th minute to open the scoring with a first-time shot that went through Raphael Varane's legs and beyond Thibaut Courtois, then added a second five minutes later after Courtois parried his effort into the path of Varane for an own goal.
Manor Solomon rifled a third with 42 minutes gone after Tete had again been the instigator, providing the forward with ample time to pick his spot.
The last visitors to score three in a first half at Madrid had been Bayern Munich in February 2000, and Zidane would have implored his side to keep better tabs on Marcos Antonio, whose rampaging runs were instrumental to Shakhtar's hefty advantage.
Zidane's words to his shellshocked players clearly had an impact as former Ballon d'Or winner Luka Modric scored with a superb long-range strike nine minutes after the break and Vinicius Junior pounced on slack possession to add a second just before the hour mark.
Shakhtar thought they had held out, then had their hopes seemingly shattered as Federico Valverde scored an apparent equaliser in extra-time.
There was one last twist, though, as the goal was ruled out for offside – a cruel end to a night to forget for Madrid ahead of El Clasico against Barcelona on Saturday.
The result meant that Madrid lost at home to a Ukrainian side for the first time in their history and began their campaign bottom of the table ahead of tests against Borussia Monchengladbach and Inter Milan in Europe.
For all the determination they showed to right a dreadful start, Madrid's scorers were realistic about the quality of their performance.
"We weren't good enough," rued Modric. "We played better in the second half but it wasn't enough.
"We know that Shakhtar are a good side and we didn't underestimate them. Simply put, we didn't start well, they scored the first goal and we let our heads drop."
Forward Vinicius Junior echoed the Croatia star. "We didn't play well," he conceded. "We're all in this together but it's tough to talk today.
"Nobody did things well and we couldn't do what the boss asked us to."
Castro was understandably thrilled with a victory that might have been as much of a turn-up to him as it was to startled viewers around the world.
"We knew what difficulties we could expect and planned our strategy accordingly," he said.
"The players have done everything absolutely fantastically. We were a united team from the first until the last minute.
"The first half was our best this season. We created chances and we could have scored more in the second half as well.
"When the score was 3-2 we had to defend even more and thought, 'oh, let this game end as soon as possible'. Overall, we showed our quality in terms of tactics and skill."
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