Six greatest Champions League upsets after Sheriff Tiraspol's win at Real Madrid

European giants Real Madrid were stunned at the Bernabeu by minnows Sheriff Tiraspol on Tuesday night - with the Moldovan champions snatching a late 2-1 win.

The 13-time European champions had drawn level through Karim Benzema after falling behind to a Jasurbek Yakhshiboev goal in the first half.

But a stunning volley from Sebastian Thill in the final minute saw Sheriff secure a famous victory - and sealed one of the biggest shocks in Champions League history.

Here, Mirror Football takes a look at six of the biggest upsets in European history following Sheriff's late, late show at the Bernabeu.

1) Real Madrid 1-2 Sheriff Tiraspor (2021)

Sheriff Tiraspol's Sebastien Thill celebrates his remarkable winning goal against Real Madrid ( Image:

REUTERS)

Sheriff's heroics in Madrid will go down in history as one of the biggest Champions League upsets in history, if not, ever.

Despite enjoying the majority of possession and peppering Sheriff's goal for the majority of the match, Madrid failed to overpower Sheriff.

This is the first-ever time the Moldovan champions have qualified for Europe's biggest competition.

And they're making light work of it, too.

Tuesday night's clash with the 13-time winners was actually Sheriff's 10th game in Europe this season, with the Moldovan outfit having to come through four rounds of qualifiers to make the group stage.

They now sit proudly atop Group D after stunning Shaktar Donetsk last month - and they have a real chance of qualifying from a group that also includes Italian champions Inter Milan.

2) Celtic 2-1 Barcelona (2014)

Was Sheriff Tiraspol's win over Real Madrid the greatest Champions League shock ever? Comment below.

Tony Watt celebrates after scoring his historic goal for Celtic against Barcelona ( Image:

Stu Forster)

Celtic enjoyed one of their most famous nights in Europe at Parkhead back in 2014.

Five-time European champions Barcelona rolled into town and nobody expected anything other than a drubbing for the hosts.

But somehow, Celtic found a way to stun their Spanish visitors.

Despite being peppered for most of the game, Celtic took the lead through Victor Wanyama and then hit Barca on the break after a long punt from goalkeeper Fraser Forster. Tony Watt would then etch his name into Celtic history forever by netting the pivotal second goal to send Glasgow wild.

Lionel Messi grabbed a late goal for a Barca side who would go on to reach the semi-finals.

But it wasn't enough to deny a stubborn Celtic side, who made a mockery of their 16% possession to emerge as victors on the night.

3) Barcelona 1-2 Rubin Kazan (2009)

The Rubin Kazan side that shocked Barcelona at the Camp Nou in 2009 ( Image:

David Ramos/Getty Images)

Barcelona were on the end of another upset five years earlier in the Champions League group stage.

Back in 2009, Russian outfit Rubin Kazan ventured into the Camp Nou against Pep Guardiola's squad of superstars.

Few would have backed Kazan against Madrid, but they took the lead in just the second minute through a stunner from Alexander Ryazantsev.

Zlatan Ibrahimovic hit back for the hosts, but Kazan rallied and snatched a victory that rocked world football through Gökdeniz Karadeniz - leaving Barca red-faced.

4) BATE Borisov 3-1 Bayern Munich (2012)

Aleksandr Pavlov celebrates the opening goal in BATE Borisov's famous win over Bayern Munich in 2012

Perhaps one of the most unusual upsets in Europe came in 2012.

Bayern Munich lifted the famous trophy that year - but that didn't look likely early on after being embarrassed right at the start of their Champions League journey by BATE Borisov.

The Belarusian side took a shock 2-0 lead through goals from Aleksandar Pavlov and Vitali Rodionov.

Munich struggled to break Borisov down but did give themselves a glimmer of hope thanks to Frank Ribery's late goal.

But a 94th-minute goal from Renan Bressan was enough to clinch the win for the side from Belarus against the European champions-elect.

5) APOEL Nicosia 1-0 Lyon (2012)

APOEL Nicosia players celebrate sealing their spot in the Champions League quarter-finals back in 2012 ( Image:

JACK GUEZ/AFP via Getty Images)

2012 was quite the year for shocks in Europe, as APOEL Niocia proved with their remarkable run to the Champions League quarter-finals.

The unfancied Cypriot side's unlikely march to the final eight saw them spark wild scenes by upsetting French giants Lyon.

Lyon headed into the second leg with a 1-0 aggregate lead, but a 1-0 win for Nicosia on the night saw the tie progress all the way to penalties.

And Dionisis Chiotis made himself a hero by thwarting Alexandre Lacazette from the spot to seal Nicosia's spot in the quarter-finals.

Nicosia vice-president Theo Kyriakides tried to sum up the extent of their achievement.

"We have a budget of around 9m euros," he told BBC radio 5 Live. "The maximum amount of money we have spent for the last four years was 1.2m euros for three players altogether. Lyon spent more than 140m euros in the last two years on transfers so you can see the extent of our achievement."

6) Barcelona 2-3 CSKA Moscow 3 (1992)

Both Ronald Koeman and Pep Guardiola were in the Barcelona team that were stunned by CSKA Moscow in 1992 ( Image:

GERARD JULIEN/AFP via Getty Images)

Barcelona in the nineties boasted a roster that other sides amongst Europe's elite could only dream of having.

However, the likes of Guardiola, Ronald Koeman and Michael Laudrup were all left stunned after Barca were dumped out of the competition by CSKA Moscow.

A 1-1 draw in Russia in the first leg had left the La Liga giants with work to do, but they were shocked in their own backyard by CSKA Moscow.

The Russian side came out on top on a remarkable night in Catalona - ultimately emerging as 3-2 victors after being 2-0 down thanks to goals from Evgeniy Bushmanov, Denis Mashkarin and Dmitriy Karsakov.