Paraguay’s longshot win against Germany in the Round of 32 is the latest in a long line of World Cup knockout boilovers.Monday’s action in the FIFA World Cup 2026 added another chapter to the book of all-time knockout upsets in the tournament, with title contenders Germany stunned by Paraguay at the round of 32 stage, adding yet more spice to an event that has already delivered plenty of drama at the group stage.Al Jazeera takes a look at the top five upsets in World Cup knockout history:Recommended Stories list of 4 itemslist 1 of 4Can Ivory Coast spoil Norway’s party in the World Cup’s round of 32?list 2 of 4VIDEO: World Cup Day 19: Morocco beats Netherlands; Germany crashes outlist 3 of 4Morocco beat Netherlands in last-32 shootout to march on again at World Cuplist 4 of 4Brazil beat Japan with injury-time winner to reach World Cup last 16end of list1. Germany vs Paraguay (2026)Jose Canale wrote his name in the history books, steering longshots Paraguay to a thrilling shootout win over four-time champions Germany in the round of 32 of the 2026 World Cup.Many thought Paraguay would be sent home packing after the group stage when the USA thrashed them in their tournament opener, but the South Americans turned their pain into purpose in no time, knocking out Germany 4-3 on penalties for the biggest upset in World Cup knockout history.Paraguay’s Jose Canale celebrates scoring the spot-kick, which helped them advance to the round of 16 [Amanda Perobelli/Reuters]2. Germany vs Bulgaria (1994)Germany have been on the receiving end of more than one knockout upset – and this one dates back to the 1994 World Cup on American soil.In their first-ever and only meeting at the World Cup, minnows Bulgaria toppled the defending champions in the quarterfinals, sealing a come-from-behind 2-1 victory over Germany that went down as one of the biggest shocks of the competition.Bulgaria’s Yordan Letchkov celebrates after scoring their second goal of a 2-1 quarter-final win over Germany at the 1994 World Cup [File: Peter Morgan/Reuters]3. Italy vs South Korea (2002)A rare golden goal decided Italy’s fate at the 2002 World Cup when co-hosts South Korea knocked them out in the round of 16.The Italians got off to a promising start when Christian Vieri gave them an early lead, but South Korea’s Seol Ki-Hyun struck a late equaliser, and Ahn Jung-Hwan sealed the deal, becoming the third of just four to score a golden goal at the global finals.The 2-1 victory helped South Korea achieve a deep run at the tournament as they finished fourth, their best result in the World Cup to date.South Korea’s Seol Ki-Hyun celebrates after they knocked out Italy in the round of 16 of the 2002 World Cup [File: Tony O’Brien/Action Images]4. Brazil vs Germany (2014)Germany handed Brazil an infamous 7-1 semifinal thrashing at the 2014 World Cup, breaking Brazilian hearts on their own soil.Five players found the net for Germany, with Oscar netting a 90th-minute consolation for Brazil – capping a humiliating result which left Brazil coach Luiz Felipe Scolari calling it the “worst day of my life”.Germany went on to win that tournament, lifting their fourth world title.Brazil players David Luiz (4) and Luiz Gustavo (right) react after being thrashed by Germany in the 2014 World Cup at Mineirao Stadium [File: Tim Groothuis/Witters Sport via USA TODAY Sports]5. Morocco vs Portugal (2022)Morocco – who stunned the Netherlands on Monday to reach the round of 16 – are no strangers to pulling off an upset, especially against European teams.At the 2022 World Cup in Qatar, the Atlas Lions tamed Cristiano Ronaldo-led Portugal, beating them 1-0 in the quarterfinals despite finishing the game with 10 players.The monumental victory saw Morocco become the first African and Arab side to reach the World Cup semifinals.Portugal’s Cristiano Ronaldo was dejected after his team were stunned by Morocco [Paul Childs/Reuters]