Paraguay 1-1 Germany (4-3 penalties) Four-time champions Germany crashed out of the FIFA World Cup in stunning fashion on Monday after suffering a shock penalty shootout defeat to Paraguay in the round of 32, one of the biggest upsets in the tournament's history. Paraguay held their nerve to win the shootout 4-3 after the sides battled to a 1-1 draw through extra time, ending Germany's title hopes at the first knockout hurdle and sending the South Americans into the last 16. The Germans produced a lifeless first-half display and fell behind just before the break when Julio Enciso rose highest to head home in the 42nd minute. Germany responded with greater urgency after half-time and were back on level terms eight minutes into the second half when Kai Havertz finished clinically to restore parity. The four-time world champions thought they had completed the turnaround midway through the second period when they found the net from a corner, but their celebrations were cut short after a VAR review ruled the goal out for a foul on Paraguay goalkeeper Carlos Coronel. With neither side able to find a winner in normal or extra time, the contest was decided from the penalty spot. Germany's hopes suffered an immediate blow when Havertz, fresh from helping Arsenal end their 22-year wait for the English Premier League title this season, saw his opening penalty saved. The Europeans went on to miss three of their five spot-kicks, while Paraguay, despite missing two of their own, held their composure to secure a famous 4-3 shootout victory. Ranked 10th in the latest FIFA rankings heading into the tournament, Germany were overwhelming favourites against a Paraguay side ranked 41st. Their elimination will go down as one of the greatest shocks in World Cup history and arguably the biggest upset ever seen in the knockout stages. Germany's previous most painful World Cup upset came at the 1994 tournament in the United States, when Hristo Stoichkov inspired Bulgaria to a memorable quarter-final victory over the defending champions. Bulgaria were ranked 29th in the world at the time, making Paraguay's triumph even more remarkable on paper. The defeat also marked another unwanted milestone for Germany, who lost a World Cup penalty shootout for the first time in their history. It continues a disappointing run for one of international football's traditional powerhouses, who have now failed to progress beyond the last 16 in every World Cup since lifting the trophy in 2010. For Paraguay, meanwhile, it was a night that will be remembered for generations. Built on defensive resilience, tactical discipline and nerves of steel from the penalty spot, the South Americans pulled off a famous victory to keep their World Cup dream alive and book a place in the last 16.