We’ve seen some of the biggest Champions League shocks over recent years.

When you get the best football teams from around Europe together in one competition, the gap between the top clubs and those just happy to be there is razor thin, all things considered.

While usually it’s one of the favorites that prevails in the end, that doesn’t mean along the way there aren’t always a number of shock upsets that nobody sees coming. This is part of the reason why betting on Champions League football is so popular–trying to guess which favorite is going to get upset unexpectedly by an underdog only adds even more excitement to the gripping tournament.

Biggest Champions League shocks

Below are five of our biggest Champions League shocks that punters and supporters alike will always remember.

Monaco 3-1 Real Madrid (2004 Quarterfinals)

The 2004 Champions League Final of Monaco vs. Porto was perhaps the most unexpected one in modern European Championship history. For that matchup to have been possible, a number of shock results had to occur along the way. Perhaps most memorable of those came in the quarterfinals between Monaco and Real Madrid, the latter of whom had dropped only two points during the group stage.

Four second half goals in Leg 1 gave Madrid what looked to be a comfortable lead for the sequel match, especially when Madrid remained up 5-3 on aggregate at halftime. But two second half goals in less than 20 minutes would tie the total score and send Les Rouges et Blancs through on the away goals rule.

Inter 1-5 Arsenal (2003 Group Stage)

Despite fielding much of the team that would later finish the domestic season undefeated and be dubbed “The Invincibles” just a few months later, Arsenal began their 2003-04 Champions League campaign clunkily, getting just one point from their first three group stage matches, including a 0-3 drubbing from Inter in London.

Although Arsenal finally gained a group stage the previous gameweek, a similar pounding was expected when the Gunners visited San Siro in late November, especially since they were without captain Patrick Vieira. Tied 1-1 at half, a 49th minute Freddie Ljungberg goal gave Arsenal a slight edge before the floodgates opened: in a span of less than five minutes, the Invincibles added three more, keeping their knockout stage dreams intact.

Sports Betting On Shock Outcomes

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Dynamo Kyiv 2-0 Real Madrid 0 (1999 Quarterfinals)

Defending European champions Real Madrid looked like they were poised to make another run to the title again in the 1998-99 edition of the competition. Even though they finished second in their group, they were still the group stage’s highest-ranked runner-up and drew a seemingly favorable matchup in the quarterfinals (there was no round of 16 back then) against Dynamo Kyiv.

But ‘favorable’ doesn’t mean much on paper, especially when the Ukrainian club had one of Europe’s biggest future superstars on their side. Andriy Shevchenko scored once in the first leg, which was equalised by Madrid minutes later. With an even aggregate for the return leg in Kiev, the future AC Milan standout would score two more, sending his side thru to the semis.

APOEL 1-0 Lyon (2012 Round of 16)

Even though their group was one of the softer ones overall in the 2011-12 UEFA Champions League, few expected APOEL FC to be one of the 16 clubs to still be alive after the group stage. The small Cypriot club had to play their way into the group stages via the qualification round, meaning their already long and grueling European season (due to having to travel further than most countries) began in July that year.

But somehow, Thrylos won their group by GD despite losing 0-2 on the last matchday of the stage, and drew Lyon, the third place team from Ligue 1 that previous year. The French side won the first leg just by 1-0 on their home soil, which APOEL happily followed up with a 1-0 regulation victory of their own on the return leg. This sent the tie to penalties, where the Cypriots converted all four of their takes and had keeper Dionisis Chiotis save two, sending the tiny club into the quarterfinals for the first time ever.

Deportivo La Coruna 4-0 Milan (2004 Quarterfinals)

Because they aren’t one of the ‘traditional’ Spanish or European club powers, it’s easy to forget that Deportivo La Coruna was a formidable side around the turn of the century that could hang with anyone on the continent. That said, in the 2003/04 Quarterfinals few expected Depor to be competitive with the Italian club that was one of the favorites to win the tournament, especially after they won the first leg 4-1 in San Siro.

No team in the history of the 12-year tournament at that point had overcome a three-goal deficit after the first leg before, and to make matters bleaker for the Branquiazuis, the defending champions Milan had yet to concede a European goal on the road that season. So when a first half onslaught had the hosts up 3-0, and a fourth was added late in the match to send Deportivo through to the semis, it’s hard to argue who was in disbelief the most: Milan players and supporters, or the rest of the football world.