1Sheriff Tiraspol beat Real Madrid 2-1 at the Bernabéu (2021)
No. 1 — Sheriff Tiraspol beat Real Madrid 2-1 at the Bernabéu (2021). On the lists of 5 of 5 AIs; median place there: 1. The AIs put it first because Sheriff had the lowest win chance ever recorded, about 30/1, and still beat Real despite Real's 31 shots.

Did you know
Sheriff's winning goalscorer Sebastien Thill had played on loan last year for FC Tambov, a Russian club that was dissolved in May 2021 after declaring bankruptcy.
- What it is
- Moldovan club Sheriff won 2-1 at Real Madrid in the 2021 group stage.
- Its edge
- It has the lowest win chance of the three: 1.4%, about 30/1.
- Who should know
- Useful for anyone who wants to know how extreme a football upset can get.
- Pre-match win chance1.4% win chance (about 30/1)
Why it is here
Real Madrid had 31 shots, 11 on target. Sheriff had only three on target and scored with two of them. Their goalkeeper made ten saves. That gap between chances and result is why this upset tops the list. — ESPN
Sheriff were the first Moldovan club in the Champions League group stage. They had started in the first qualifying round and needed eight games to get there. Real Madrid were 13-time winners, so the gap in status was huge. — Goal
Did you know
The 2021 match was Sheriff's first Champions League group-stage season, and the club was only founded in 1997. They had already won both of their first two group games before travelling to Madrid.
History
Sheriff won its first Moldovan league title in 2000–01, the start of a run of ten straight titles up to 2010. The club is owned by a Transnistrian business conglomerate.
Keep in mind
Real's own coach felt robbed: Carlo Ancelotti said, "We lost and we didn't deserve it." ESPN also blamed easy goals and loose defending, so this win owed something to Real's mistakes.
Sheriff is run by a company that owns petrol stations, supermarkets and a phone network in Transnistria, a region the UN still counts as part of Moldova. Its stadium cost around £148m.
What people say
We believed we could win. I spoke to my teammates as captain, motivating them, saying 'why not dream?' — Frank Castaneda, Sheriff captain
Where to go further
Open the match page and check the shot count first. Real Madrid had far more shots than Sheriff. Then read the timeline: Sheriff scored first, and Real Madrid equalised from a penalty.
Video: 2021, in 6 minutes · Vox
