Champions League debutants Sheriff pulled off one of the biggest upsets in the competition s history by stunning Real Madrid at the Santiago Bernabeu with a dramatic 2-1 victory.
Jasurbek Yakhshiboev s first-half header was cancelled out by Karim Benzema s spot-kick after the break, given following a VAR check after Vinicius Junior went down in the box.
However, it was the visitors who claimed a remarkable win to maintain their 100 per cent record in Group D, Sebastien Thill s stupendous left-footed strike in the 89th minute earning the Moldovan club their most famous triumph.
Los Blancos subjected the minnows to a 31-shot barrage, with goalkeeper Georgios Athanasiadis forced into 10 saves, but the competition s most successful team were unable to salvage anything from the contest on a fairytale night for Sheriff.
The hosts were left stunned when Sheriff took the lead in the 25th minute with their first shot of the game. A piercing pass released Cristiano into acres of space, allowing the left-back to dink a cross to the back post that Yakhshiboev headed powerfully across Thibaut Courtois and in.
Sheriff s goalscorer could have doubled his tally and his team s advantage six minutes later, but his left-footed effort curled just wide of the far corner.
Vinicius and Nacho spurned terrific opportunities to level the scores within 60 seconds of each other as the former s casual finish drifted past the top-right corner and the latter somehow headed a rebound from an Eden Hazard shot over the top with the goal gaping.
Benzema then thumped narrowly wide from the edge of the box and Casemiro forced a smart save from Athanasiadis, but the away side went into the break ahead.
Madrid finally restored parity as Vinicius was felled in the box, with Benzema converting emphatically from 12 yards in the 65th minute.
The hosts poured men forward in search of a winner, but it was Sheriff who incredibly found the decisive late goal as Thill fired a rocket of a strike into the top-left corner from the edge of the box with just a minute of normal time remaining.
What does it mean? Sheriff upsetting all the odds
Sheriff become the first team since Leicester City in 2016-17 to win their first two games in the competition after beating Shakhtar Donetsk 2-0 in their opening fixture.
The Moldovan side were widely expected to finish bottom of a group that also includes reigning Serie A champions Inter, but are top of the table with six points three points ahead of second-placed Madrid after a victory they perhaps could not have even dreamt of.
Benzema marks half-century with goal
The France striker made his 50th Champions League appearance at the Bernabeu in Real Madrid colours and marked a special personal occasion with his penalty, taking him to 36 home goals for the club in the competition only Cristiano Ronaldo (54) and Raul (46) have more. However, it was not a night he will want to remember as Sheriff ensured it counted for nothing.
Madrid denied 100th home win
Victory over Sheriff at the Bernabeu would have meant Los Blancos made history as the first side to record 100 home wins in the competition, but their shock defeat to a stubborn, clinical opponent means Carlo Ancelotti s men will have to wait until the clash with Shakhtar on November 3 for another chance to reach that milestone.
What s next?
Real Madrid must try to wrestle control of the group back from Sheriff and cannot afford to slip up in their next European game, away to Shakhtar. Sheriff, meanwhile, travel to Italy to face Inter in the hopes of making it three wins from three. In the more immediate future, Madrid visit Athletic Bilbao in LaLiga on Sunday, a day after Sheriff face leaders Milsami in domestic action.