Were does Sheriff’s win at Real Madrid rank in the biggest Champions League shocks of all-time? 

If anyone thinks the Champions League is all about the biggest and best teams in Europe, tell them to think again after watching Sheriff Tiraspol on Tuesday night.

Moldovan minnows? Not in the slightest. The Champions League debutants stunned the mighty Real Madrid – who have won this competition more times than anyone else – 2-1 in their own backyard in one of football’s biggest shocks. 

The result not only gives every single team in this tournament, irrespective of history or stature, a chance in every single match they play in, but it makes a complete mockery of the European Super League debate that arose this year.

With Sheriff still celebrating, Sportsmail looks at where this result sits in terms of the biggest shocks the Champions League has ever seen…  

Moldova’s Sheriff Tiraspol beat Real Madrid 2-1 away in the Champions League on Tuesday

Sportsmail looks at where Sheriff's shock win ranks in the all-time Champions League shocks

Sportsmail looks at where Sheriff’s shock win ranks in the all-time Champions League shocks

10. Newcastle 3-2 Barcelona – 1997

One reform that has actually helped European club football was the introduction of placing other teams from domestic leagues, not just the champions, into the tournament in 1997.

Before that year, the Champions League was a closed shop to the winners of their respective European leagues but 1997 saw the tournament expand from just 24 teams to a whopping 55.

Newcastle took on a Barcelona side that included Rivaldo in it at St James' Park back in 1997

Newcastle took on a Barcelona side that included Rivaldo in it at St James’ Park back in 1997

Runners-up from the top eight domestic leagues were allowed to play at Europe’s top table, along with champions from smaller domestic leagues. 

Newcastle were one of the beneficiaries of the new rule, as their second-placed finish that year earned them a spot in the tournament – with the club breezing through their second qualifying round to take on Barcelona in their first group stage game. 

The clash at St James’ Park was nothing short of memorable with the likes of Rivaldo, Luis Figo and Luis Enrique rocking up at St James’ Park for their European bid.

Faustino Asprilla (above) hit a hat-trick in just 49 minutes to seal a 3-2 win for the Magpies

Faustino Asprilla (above) hit a hat-trick in just 49 minutes to seal a 3-2 win for the Magpies

But it was the great Newcastle entertainers who stole the show that night, with Faustino Asprilla hitting a hat-trick within 49 minutes to put the Magpies 3-0 up.

Enrique and Figo hit late consolation strikes but the damage was already done. 

Unfortunately for Newcastle, they would fail to win their next four group stages and a third-placed finish saw them crash out of the competition. 

9. Helsingborgs 1-0 Inter Milan – 2000 

Two decades ago, Sweden never had a side competing in the Champions League group stages – until Helsingborgs managed to complete that feat in dramatic fashion.

Not many gave the Swedish minnows a chance against the might of Inter Milan in the third qualifying round. They had a ground of just 16,500 capacity compared to the top-quality San Siro stadium Inter had.

Meanwhile, Marcello Lippi’s Inter lined up for the first-leg in Sweden with the likes of Laurent Blanc at the back, Andrea Pirlo in midfield and new signing Robbie Keane up front.

An Inter Milan side with Robbie Keane (above) in it was beaten 1-0 by Sweden's Helsingsborgs

An Inter Milan side with Robbie Keane (above) in it was beaten 1-0 by Sweden’s Helsingsborgs

But Helsingborgs stunned Inter with Michael Hansson’s late winner with eight minutes to go giving the Swedish minnows a shock first-leg lead.

Surely that was overturned in the second leg at the San Siro? Absolutely not. Helsingborgs hung on for a 0-0 draw a fortnight later and Inter were dumped out of the Champions League before the proper stage of the tournament had already begun. 

8. Brondby 2-1 Bayern Munich – 1998

The 1998-99 season ended in heartache for Bayern Munich, with Teddy Sheringham and Ole Gunnar Solskjaer scoring late goals in the Champions League final to earn a 2-1 win for Manchester United and break German hearts.

Perhaps Bayern should have learned their lessons from their first group stage match of that European season, when they were humbled by Danish side Brondby on the way to the final. 

With the likes of Carsten Jancker and Lothar Matthaus travelling to Denmark, it was expected that Bayern would walk over Brondby, who were generally seen as the whipping boys of the group with the German giants, Manchester United and Barcelona.

German giants Bayern Munich were beaten by Denmark's Brondby on the way to the 1999 final

German giants Bayern Munich were beaten by Denmark’s Brondby on the way to the 1999 final

It certainly looked like Bayern were going to get all three points when Markus Babbel put them 1-0 up late on, but goals in the 87th and 90th minute sealed a shock turnaround for the Danes. 

Thomas Helmer’s own goal was swiftly followed up by Allan Ravn’s injury-time strike to send Brondby into dreamland. 

How did this story end? Brondby went on to lose their remaining five matches and ended up on a goal difference of minus 14. 

7. Barcelona 1-2 Rubin Kazan – 2009

Rubin Kazan were not even a Russian top-flight side until 2003, let alone playing in the Champions League.

But the Russian minnows won their country’s top-flight in 2008 to secure a spot in the Champions League proper the following year.

Their first ever group stage campaign in Europe’s premier club competition could not have been harder, with reigning champions Barcelona pitted against them along with Jose Mourinho’s Inter Milan – who went on to win the treble that season.

Rubin Kazan stunned reigning European champions Barcelona 2-1 back in late 2009

Rubin Kazan stunned reigning European champions Barcelona 2-1 back in late 2009

Nobody gave Kazan a chance when they travelled to Barcelona, with Pep Guardiola picking Lionel Messi and Zlatan Ibrahimovic as forwards, with Xavi, Andres Iniesta, Dani Alves and Yaya Toure also in the Catalans’ team.

But the collection of Barcelona stars were humbled after just 120 seconds when Aleksandr Ryazantsev hit a 30-yard thunderbolt after Rafael Marquez’s misplaced pass at the Camp Nou.

The Catalans hit back after half-time when Ibrahimovic levelled the scores but the Russians were not done there yet. Gokdeniz Karadeniz fired in a winner with 15 minutes to go to earn Rubin a shock triumph at the home of the European champions. 

Zlatan Ibrahimovic (left) scored for the Catalans but Pep Guardiola's all-star team were beaten

Zlatan Ibrahimovic (left) scored for the Catalans but Pep Guardiola’s all-star team were beaten

Guardiola (far right) was ousted by Rubin Kazan coach Kurban Berdyev (second right)

Guardiola (far right) was ousted by Rubin Kazan coach Kurban Berdyev (second right)

Barcelona had 22 shots that night compared to Rubin’s three, but the Russian side’s clinical nature saw them come up trumps in Spain.  

What’s more – Rubin even managed to hold Guardiola’s Barcelona to a 0-0 draw in the return fixture, as the Russians picked up five points overall to move into the Europa League. 

6. APOEL 1-0 Lyon – 2012

Cypriot club APEOL Nicosia started their 2011-12 Champions League campaign at the second qualifying round but were handed a relatively easy set of draws, including in the group stages.

The European minnows managed to finish top of their Champions League group against tournament regulars FC Porto, Zenit Saint Petersburg and Shakhtar Donetsk to make it through to the knockout stages.

They were given a reasonably favourable draw against French side Lyon, one of the biggest sides in France in the days before PSG’s rise to dominance. 

Cypriot side APOEL Nicosia stunned Lyon in the 2012 campaign to reach the quarter-finals

Cypriot side APOEL Nicosia stunned Lyon in the 2012 campaign to reach the quarter-finals 

Remi Garde’s side possessed the likes of Hugo Llloris, Alexandre Lacazette, Lisandro Lopez, Yoann Gourcuff and Dejan Lovren in their side – among others – making it APOEL’s biggest challenge in their history.

But the side with just £9million in overall club budget managed to hang on to a 1-0 defeat in the first-leg before taking the game to extra-time in the second thanks to a 1-0 win from Gustavo Manduca’s goal. 

A 4-3 penalty shootout win put APOEL into the quarter-finals and the town of Nicosia was partying well into the night.

The Cypriot side managed to get a dream draw of Real Madrid in the last eight, but were thrashed 6-2. 

5. BATE Borisov 3-1 Bayern Munich – 2012

Bayern Munich were out for Champions League revenge in the 2012-13 season after losing the previous season’s final to Chelsea on their home turf. 

The German champions would go on to win the treble that season under Jupp Heynckes but were certainly given a scare by Belarusian side BATE Borisov in the group stages. 

The Belarusian side had never won a Champions League home game in their history – and when Bayern showed up in Minsk with the likes of Thomas Muller, Franck Ribery and Toni Kroos in their team, that run was set to continue.

BATE Borisov won their first ever Champions League home game by beating Bayern Munich 3-1

BATE Borisov won their first ever Champions League home game by beating Bayern Munich 3-1

But Bayern, who had won every game of the season up until that point, fell behind to Aleksandr Pavlov’s low first-half strike, before Vitali Rodionov found the top corner to double their advantage. 

Ribery managed to halve the deficit to make things nervy for BATE but Renan Bressan scored a third in injury time to seal the points. 

The result took BATE top of their group on six points after two games, but four defeats saw them slip into third, where they went into the Europa League behind eventual winners Bayern and second-placed Valencia.  

4. Dynamo Kiev 2-0 Real Madrid – 1999

The 1999 season was a historic year for Manchester United, who won the treble that year, but it could have easily been Dynamo Kiev who completed that feat instead of Sir Alex Ferguson’s men. 

Under legendary tactical manager Valeriy Lobanovskyi, Dynamo won the Ukrainian domestic double and found themselves in the latter stages of the Champions League after a dream run. 

Dynamo managed to get past Arsenal in the group stages before being paired with Real Madrid in the quarter-finals.

John Toshack’s side had the likes of Raul, Samuel Eto’o, Clarence Seedorf and Roberto Carlos in their team, but were stunned by the Ukrainians in the last eight.

Andriy Shevchenko (right) scored twice for Dynamo Kiev to knock Real Madrid out in 1999

Andriy Shevchenko (right) scored twice for Dynamo Kiev to knock Real Madrid out in 1999

A 1-1 draw at the Santiago Bernabeu set things up nicely for the return fixture in Kiev, where Andriy Shevchenko’s double got Dynamo over the line and into the semi-finals.

The run would end at the hands of Bayern Munich who beat them 4-3 in the last four, but Dynamo ran them pretty close as well.  

3. Celtic 2-1 Barcelona – 2012

Nobody, absolutely nobody, gave Celtic a chance against Barcelona when the Catalans visited Parkhead in the autumn of 2012. 

Tito Vilanova’s side had been rampant at the beginning of the season and that showed in the opening exchanges of the game. 

Tony Watt (left) scored a historic goal in a 2-1 win for Celtic over Barcelona back in 2012

Tony Watt (left) scored a historic goal in a 2-1 win for Celtic over Barcelona back in 2012

Barcelona restricted the Scottish giants to just 11 per cent possession all game and Neil Lennon’s side were camped on the edge of their own box for most of the game. 

But football, eh? Celtic took the lead in the first-half through Victor Wanyama’s goal and the pressure from Barcelona intensified. Vilanova’s Catalans ended up recording 23 shots overall, including 14 on target, but Fraser Forster was a tough man to beat.

As Barcelona pushed forward, 18-year-old striker Tony Watt scored the goal of his dreams, bursting through on goal to slide past Victor Valdes and put Celtic 2-0 up. 

Cue pandemonium at a raucous Celtic Park that Lionel Messi described as one of the best atmospheres in football. 

Lionel Messi (middle) described the Parkhead atmosphere as one of the best in football

Lionel Messi (middle) described the Parkhead atmosphere as one of the best in football

Fraser Forster was branded as the 'Great Wall' by Spanish media after making 14 saves

Fraser Forster was branded as the ‘Great Wall’ by Spanish media after making 14 saves

Celtic goalkeeper Forster was forced to make 14 saves throughout the match, with Spanish media calling him ‘The Great Wall’.

Messi eventually found a way through in stoppage time but it was just a consolation. 

Celtic had beaten Barcelona and it even reduced Sir Rod Stewart to tears in the crowd. 

2.  Deportivo La Coruna 4-0 AC Milan – 2004

AC Milan were Champions League holders in 2003 and looked set for another decent crack at regaining their title the season afterwards. 

The Rossoneri went 4-1 up on aggregate in their quarter-final tie against Spanish side Deportivo La Coruna and were looking on course for the final once again. 

But a wild night in Spain saw Carlo Ancelotti’s side lose their lead in the space of 43 minutes thanks to goals from Walter Pandiani, Juan Carlos Valeron and Albert Luque. 

The likes of Andriy Shevchenko, Kaka, Paolo Maldini, Clarence Seedorf and Cafu were completely stunned by that first-half and were unable to control what was happening in the return leg. 

Deportivo La Coruna came from 4-1 down on aggregate to beat AC Milan 5-4 back in 2004

Deportivo La Coruna came from 4-1 down on aggregate to beat AC Milan 5-4 back in 2004

The turnaround was completed when midfielder Fran netted with 15 minutes to go to seal one of the greatest comebacks in Champions League history. 

Deportivo would go on to lose to eventual winners FC Porto in the next round in a season that belonged to the European underdogs. 

1. Real Madrid 1-2 Sheriff Tiraspol – 2021

But none of the above shocks come close to Sheriff’s stunning win in Madrid on Tuesday night.

Never before had Moldova, let alone the Tiraspol club, submitted a team into the Champions League group stages but the minnows managed to beat the most successful team ever in the competition. 

Sheriff's shock win over Real will surely go down as the greatest shock in European football

Sheriff’s shock win over Real will surely go down as the greatest shock in European football

Real are not at their all-time best at the moment but the likes of Karim Benzema, Vinicius Junior and Eden Hazard were surely strong enough to get past the Moldovans. 

Both of Sheriff’s goals came from loanee players Jasurbek Yakhshiboev and Sebastien Thill, the latter having a tattoo depicting him dreaming of the Champions League on his leg. 

The result leaves Sheriff top of their group on six points after they beat Shakhtar Donetsk in their first game. This story is far from over yet… 

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