From Alcorcón To Pordenone: The Biggest Cup Upsets In Footballing History

Everybody loves a good cupset; these are the best.

Soccer is one of the very few sports that boasts competitions where small, local sides are able to face off against the best teams in the country. These matchups capture the imagination while providing a sense of hope and magic to a small group of supporters.

Domestic cups have long provided smaller clubs with the opportunity to prove their mettle by facing nationally recognized sides, and while major upsets are rare, just the slightest hope of an improbable win is enough to cause local pandemonium and stir significant interest among neutral supporters.

Due to a few factors, upsets are most common in France and England, while very rare in Italy.

The Coupe de France includes every amateur and professional club in the country, 8,506 in all, while the FA Cup consists of the top 10 tiers in English soccer, a total of 736 clubs. Other cups, such as the Coppa Italia, DFB-Pokal and Copa del Rey only include the top three or four tiers and often have top clubs join late in the competition. This leads to fewer upsets and makes unexpected cup runs more difficult. 

The English footballing pyramid also arguably has the smallest talent gap between divisions of any country. A fourth or fifth-tier side in England is often equivalent to a second or third division squad elsewhere, thus making upsets between teams separated by multiple divisions more common in England.

Just this past weekend, League Two Cheltenham held a lead over Manchester City for 22 glorious second half minutes and non-league Chorley pushed Wolves to the brink

While these upsets never came to fruition, significant underdogs have come out victorious many times over the years.

Here is a list of the biggest domestic "cupsets" in footballing history.

Biggest Cup Upsets Of All Time

England

Lincoln City vs. Burnley (2016-17)

This FA Cup fifth-round tie between Premier League Burnley and fifth-tier Lincoln City was a resolute reminder that the robust football of yesteryear is still effective. The match featured two physical sides with a penchant for the long ball and an innate knowledge of the 4-4-2. Lincoln striker Matt Rhead, a burly man standing at 6-4, 234 pounds, went to war with the Burnley backline, committing five fouls and winning 17 aerial duels. The two teams battled for 88 minutes before the decisive goal by Lincoln defender Sean Raggett, confirmed by goal-line technology.

The Imps were the first non-league side in 103 years to reach the quarterfinals of England's most storied competition. Since that February afternoon, Lincoln has earned two promotions and currently sits second in the League One table. Burnley, despite what some see as "archaic" tactics, has managed Premier League survival against the odds for five seasons running.

Hereford United vs. Newcastle United (1971-72)

A cup tie that featured one replay, three postponements and a surplus of mud ended up as one of the biggest upsets in footballing history. Hereford was a member of the Southern Football League Premier Division, the seventh tier of English football, when the Bulls faced off against First Division Newcastle in an FA Cup third-round match. After a 2-2 draw at Saint James' Park, Hereford earned a replay at their historic Edgar Street ground. With tickets sold out, fans took to every vantage point to watch the match, including trees and floodlight supports.

In less-than-optimal playing conditions, Ronnie Radford's long-distance strike, considered by some to be the greatest FA Cup goal ever, forced extra time before Ricky George's finish that gave the home side a 2-1 victory in a famous upset.

"As soon as I hit it, I knew it were in," Radford, a part-time carpenter recalled. "It could've finished in the car park but it didn't; it finished in the net."

In 2010-11 the FA created the Ronnie Radford Giant-Killer Award, given to the team achieving the biggest FA Cup upset each season.

Sutton United vs. Coventry City (1988-89)

In recent years, Sutton is famous for reaching the FA Cup fifth round as a non-league side before falling to Arsenal, a match marked by 45-year-old backup goalkeeper Wayne Shaw's memorable pasty-eating incident. Sutton's giant-killing reputation was actually established three decades earlier though. In 1987-88, the Conference side reached the FA Cup third round, and the next season Sutton achieved its most illustrious FA Cup upset.

In January of 1989, the fifth-tier team welcomed First Division side Coventry City to Gander Green Lane for an FA Cup third-round match. Coventry won the cup just two seasons earlier, but experienced no such luck on this winter afternoon. Sutton manager Barrie Williams, a pipe-smoking, Shakespeare-quoting English teacher, led the GM Vauxhall Conference side to victory courtesy of two goals via corner kicks, and the Amber and Chocolates reached the FA Cup fourth round.

Honorable Mention

Wrexham vs. Arsenal (1991-92)

Arsenal, the previous season's champion, faced off against a Wrexham side that finished bottom of League Two, only saved from relegation by the expansion of the Football League. But that didn't stop the Welsh side from defeating Arsenal's star-ladden club.

Shrewsbury Town vs. Everton (2002-03)

The Shrews finished bottom of League Two and were relegated from the Football League at the end of the season, but they enjoyed one moment of glory when they defeated Wayne Rooney's Everton side.

Spain

AD Alcorcón vs. Real Madrid (2009-10)

Dubbed "Alcorconazo" by Spanish fans and press, Alcorcón's victory over Real Madrid in the 2009-10 Copa del Rey is widely considered the biggest upset in the history of Spanish football. A third-tier club at the time, Alcorcón received an easy initial draw in the competition, collecting a first round bye before defeating a pair of fourth-tier sides to advance to the Round of 32. That luck seemingly ran out in the fourth round when the village side drew the Galácticos juggernaut of Real Madrid. 

Alcorcón faced a two-leg tie against LaLiga's most expensive team, a Real Madrid side that had spent upwards of $300 million on the likes of Cristiano Ronaldo, Kaká and Xabi Alonso just months before. The average Alcorcón player earned less in a year than Ronaldo did in a day, but that didn't stop the Segunda División B side from dispatching Madrid 4-0 in the first leg before holding on for a 1-0 defeat in the second leg and a 4-1 victory on aggregate. The Guardian called it "Real Madrid's greatest humiliation," making this match perfect for our list.

UE Cornellà vs. Atlético Madrid (2020-21)

Just a season removed from losing to third-tier side Cultural y Deportiva Leonesa, Atlético experienced another shocking defeat to a third-division club, this time against even weaker opposition. Cultural was an underrated opponent, finishing second in its Segunda División B group last season and narrowly missing out on promotion. But Cornellà is currently eighth in its Segunda División B group, having gained promotion to the third-tier for the first time in 2013-14, while Atlético led LaLiga at the time.

The Catalonian hosts took the lead off of a volleyed finish from a free kick in the seventh minute and were able to stave off wave after wave of Atlético attack to secure the biggest victory in club history.

Honorable Mention

Real Madrid vs. CD Alcoyano (2020-21)

The second match on this list from the current season, this was also the second time in recent years that Madrid lost to a Segunda División B club in the Copa del Rey.

Atlético Madrid vs. Cultural y Deportiva Leonesa (2019-20)

Cultural, a third-division side, had not advanced to the Copa del Rey Round of 32 since the 1950s, but that didn't stop La Culta from upsetting one of LaLiga's top teams.

France

Clermont Foot vs. Paris Saint-Germain (1996-97)

A quarter of a century ago, PSG was not quite the global powerhouse it is now, but coming off a second-place finish in Ligue 1, the side from the French capital was a heavy favorite against Clermont Foot of Championnat National 2, the French fourth tier. A Clermont penalty in the first half gave the National 2 squad hope, but the home side was down 4-1 with 20 minutes left, and PSG seemed to be cruising toward victory.

Clermont was not finished though. Three late goals, the last an own goal in the 87th minute, allowed the hosts to send the match to extra time. A scoreless 30 minutes meant a shootout, and Clermont keeper Olivier Enjolras was the hero, saving two Parisian spot kicks to complete an improbable comeback over one of France's biggest clubs.

Calais RUFC vs. Bordeaux (1999-2000)

Perhaps the greatest run in the Coupe de France came at the turn of the century when fourth-tier Calais Racing Union FC made it all the way to the final. To reach the quarterfinals, Calais had to defeat a pair of Ligue 2 sides, Lille and Cannes, before it was paired with Ligue 1 club Strasbourg. A second-half comeback helped the fourth-tier team advance to the semifinals, where it encountered its toughest challenge yet: Bordeaux.

Bordeaux was reigning Ligue 1 champ, but it was the Championnat National 2 club that came out on top at a sold-out Stade Bollaert-Delelis. Normal time finished scoreless, yet the extra 30 minutes saw four goals scored, three of them by Calais, as the amateurs advanced to the cup final. Nearly 79,000 fans came out to see the match; Calais took an early lead but could not prevent Ligue 1 Nantes from scoring a pair of second-half goals, thus ending the fairy tale.

Honorable Mention

JS Saint-Pierroise vs. Chamois Niortais FC (2019-20)

One thing that makes the Coupe de France so charming is the number of sides that contest the cup. The competition is open to all amateur and professional clubs in France and its overseas departments — 8,506 to be exact. Réunion is a small French island in the Indian Ocean off the coast of Madagascar, making its soccer teams eligible for the cup. In January 2020, JS Saint-Pierroise travelled 6,000 miles to defeat Ligue 2 side Niort in a hefty upset, sending the Réunionese club to the Coupe de France Round of 32.

USJA Carquefou vs. Marseille (2007-08)

Carquefou was a fifth-tier club in 2007-08 when it defeated Marseille in the Coupe de France to reach the quarterfinals of the competition. 

Grenoble vs. Marseille (2014-15)

Another major upset for Marseille in the Coupe de France, Marcelo Bielsa's side was leading Ligue 1 in 2015 when it fell to fourth-tier Grenoble on penalties in the French cup.

Germany

FV Weinheim vs. Bayern Munich (1990-91)

When third-tier Weinheim of the Baden Oberliga defeated Bayern in 1990, it was the first time since 1957 that the German giants were eliminated in the first round of the DFB-Pokal. A sold-out Sepp-Herberger-Stadion welcomed a Bayern side that expected a walk in the park; instead, a first half red card and penalty meant that the Bundesliga squad trailed at the half. Despite its talent, 10-man Bayern could simply not overcome Weinheim, and the amateurs held on for a 1-0 victory.

TSV Vestenbergsgreuth vs. Bayern Munich (1994-95)

Noticing a trend here? Just four years removed from its shock defeat to Weinheim, Bayern lost in the first round of the cup again when it was defeated by third-division club TSV Vestenbergsgreuth of the Regionalliga Süd. Bayern boasted stars such as Lothar Matthäus and Oliver Kahn, but Giovanni Trapattoni's managerial debut in Germany ended in embarrassment, with another 1-0 defeat to an amateur club. 

"We have to live with the humiliation," Matthäus said after the match, while German newspaper Bild-Zeitung wrote: "The Bundesliga laughs at this joke: Giovanni Trapattoni has learned three words in German so far: Thank you, please and — Vestenbergsgreuth."

Honorable Mention

Hamburger SV vs. VfB Eppingen (1974-75)

Named Die Mutter aller Pokalsensatione (the mother of all cup upsets), following the expansion of the competition in 1963, this match was the first time an amateur side knocked out a Bundesliga side in the DFB-Pokal.

Eintracht Trier vs. Borussia Dortmund (1997-98)

Champions League winners the previous season, Dortmund could not get past third-tier Eintracht Trier in the DFB-Pokal.

Italy

Alessandria vs. Palermo and Genoa (2015-16)

Italy's domestic competition is known for the high quality of soccer but often lacks major upsets. The Coppa Italia features 78 teams from the top four divisions of the Italian pyramid, but the top eight Serie A sides receive a bye until the tournament's round of 16, meaning they rarely face inferior competition. One of the few Cinderella runs in the Coppa Italia came in 2015-16 when Serie C side Alessandria made it to the semifinals.

Alessandria defeated fourth-, third- and second-tier opposition before coming up against Serie A's Palermo in the fourth round. I Grigi (The Greys) dispatched Palermo 3-2 then came up against Genoa, another top-tier side, in the round of 16. An extra-time defeat of Genoa led Alessandria to the quarterfinals, where the Serie C club defeated second-tier Spezia to earn a semifinal matchup against AC Milan. A 6-0 aggregate defeat ended Alessandria's Coppa Italia dreams, but the club matched Bari's run in 1983-84 as the best Serie C run in the competition.

Pordenone vs. Cagliari (2017-18)

One of the few other major upsets to occur in the Coppa Italia, Pordenone did its best to match the success of fellow Serie C side Alessandria a few seasons earlier. The third-tier club had an easy draw on paper, but in reality it faced a tough route in the tournament. The Green Lizards defeated Matelica, who went on to earn promotion from Serie D, in the first round, turned a 2-0 deficit into a 3-2 victory against Serie B's Venezia in round two, then defeated Serie C champ Lecce in the next stage.

This set up a round of 16 matchup with Cagliari of Serie A. A second-half Alessandro Bassoli header advanced Pordenone to the round of 16, where it would face Inter Milan. The Green Lizards pushed Inter to the brink, but after 120 scoreless minutes, Pordenone narrowly succumbed to the Serie A club on penalties, thus ending Pordenone's magical cup run.

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