Antonio Rudiger's last-minute header shattered Shakhtar Donetsk hearts in Warsaw, with a 1-1 draw securing Real Madrid's spot in the Champions League knockout stages.
Oleksandr Zubkov opened the scoring a minute into the second half to put the Ukrainian side in sight of a sensational result on Tuesday, with the hosts close to doubling their lead when Lassina Traore clipped the crossbar.
Carlo Ancelotti's side, needing a point to secure safe passage to the round of 16, went for broke in the closing stages by moving Antonio Rudiger into a forward role.
That provided the breakthrough in the closing seconds, the German defender heading past Anatoliy Trubin to deny what would have been a famous victory.
A passive first half saw limited opportunities, Karim Benzema having the first sight of goal after 18 minutes with a stinging shot to test Anatoliy Trubin, who then enjoyed a quiet spell before tipping Federico Valverde's effort from long distance over the bar.
Shakhtar capitalised on their visitors' poor showing by taking the lead just minutes into the second period, Bohdan Mykhailichenko providing the cross for Zubkov to head past compatriot Andriy Lunin.
As below-par Madrid toiled, Shakhtar continued to pose more threat – Traore rounding Lunin but only chipping his effort against the crossbar, with Zubkov then forcing the Madrid goalkeeper into action before Mykhaylo Mudryk dragged an attempt wide.
Those missed chances ultimately proved costly, with makeshift striker Rudiger – having nodded just wide a few moments prior – heading home in the fifth minute of stoppage time to send Madrid through.
Tuchel to make Bayern Munich changes for Stuttgart ahead of Real Madrid clash
Bayern Munich travel to Stuttgart this weekend and are ready to rotate their side with the Champions League semi-final second leg at Real Madrid to come four days later, manager Thomas Tuchel said.
The league title has been secured by Bayer Leverkusen, and with the Bundesliga's top five clubs guaranteed Champions League football next season, Saturday's clash between Bayern in second and third-placed Stuttgart is not crucial.
"We will give a few players the chance to pick up some rhythm," Tuchel said at his pre-match press conference on Friday.
"Of course, we will also take a few players out and allow ourselves to adapt the rhythm to Wednesday.
"But that doesn't relieve us of our responsibility, that those who play have to fight and show grit there."
Bayern drew 2-2 at home to Madrid on Tuesday, a game Matthijs de Ligt missed due to injury, and the Dutch defender will also sit out the trip to Stuttgart in the hope of making the return game in Spain.
"Matthijs de Ligt won't be in the squad, as the plan is that he returns to training on Sunday, then we have got three days," Tuchel said.
"Jamal Musiala won't be in the squad. Same procedure there. Dayot Upamecano will try and train [Friday], so we'll see."
Leroy Sane scored in the draw with Madrid, after missing the last four league games through injury. The winger has played three Champions League games in that time and will be in the squad for Stuttgart.
"You always try to have a connection to the players. Leroy's been training with pain for seven or eight weeks, but is always available," Tuchel said.
"He has a high threshold. He deserves the utmost respect there. He's a bit short there at the moment because he can't train properly.
"But he is in training and is coming to Stuttgart."
Bayern have 69 points, five ahead of Stuttgart with three games remaining.
Saudi Pro League: Mahrez and Firmino on target as Al-Ahli tighten grip on third place
Riyad Mahrez and Roberto Firmino were both on target as Al-Ahli tightened their grip on third place in the Saudi Pro League table with a 4-1 win over Damac on Thursday.
Matthias Jaissle's team were four goals up within just 25 minutes as Damac folded, Ziyad Al Johani and Feras Al Brikan netting their first two before Franck Kessie was felled by Dhari Al Anazi for a penalty, converted by Mahrez.
Firmino then tapped home a fourth after being teed up by former Newcastle United winger Allan Saint-Maximin on the break, but Al-Ahli took their foot off the gas from there, Domagoj Antolic's second-half consolation rounding off the scoring.
Elsewhere, 10-man Al-Riyadh scored two stoppage-time draws to earn a dramatic 2-2 draw with Al-Fateh in Al-Mubarraz.
Goals from Djaniny and former Columbus Crew star Lucas Zelarayan put Slaven Bilic's hosts on the brink of victory, with Al-Riyadh playing almost half the game a player down after Khalid Al Shuwayyi's 54th-minute red card.
An astonishing collapse denied them, however, with Mohammed Al Shwirekh halving the arrears one minute into stoppage time before Didier Ndong headed in a left-wing cross three minutes later.
Thursday's other game saw Al-Hazm and Al-Akhdoud play out a goalless draw, keeping the hosts bottom of the table while Al-Akhdoud inched two points clear of the relegation zone.
Ancelotti defends Kroos substitution against Bayern Munich
Carlo Ancelotti defended his decision to substitute Toni Kroos during Real Madrid's 2-2 draw with Bayern Munich.
The two European heavyweights shared the spoils in a thrilling Champions League semi-final first leg at the Allianz Arena, where Vinicius Junior's late penalty levelled the tie.
Vinicius had opened the scoring in the 24th minute after latching onto Kroos' delicious throughball, one of a game-high 15 line-breaking passes the Germany midfielder played during the first half.
The 34-year-old was replaced by Brahim Diaz for the final 14 minutes of the contest, which Bayern had turned around thanks to second-half strikes from Leroy Sane and Harry Kane.
But Ancelotti, who knows the support of Madrid's fans will be crucial when he welcomes his former club to Santiago Bernabeu for next week's second leg, explained his thinking.
"Jude Bellingham had cramp, Toni Kroos played a spectacular game, but the plan was to try to recover the control of the game by putting fresh legs in," the Italian told reporters during his post-match press conference.
"As always, at this point in the season, we have a great opportunity to play in another final. It's an even tie against a great team. It will be another 90 minutes of suffering, but in an atmosphere that we know quite well. The fans are going to help us."
Meanwhile, Thomas Tuchel knows Bayern will have their work cut out in the second leg, but has encouraged his players to be confident and embrace the challenge.
"The situation is now very clear," he said. "We go to Madrid and the winner takes it all. We are ready to fight. It is important to believe that.
"It is still possible. It is 50-50. It is one of the toughest places to win, but that is also what makes this challenge exciting."
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