Portugal scored a beautiful goal set up by Cristiano Ronaldo with less than 30 seconds left in injury time to break the heart of American fans and earn a 2-2 tie.
Team USA was just seconds away from clinching a spot in the Round of 16, when Ronaldo centered a ball that Silvestre Varela headed in for a goal.
It was a game that was about as much must-win for both teams as possible for the second match of the group stage.
Portugal was reeling after a 4-0 thrashing by Germany; the U.S. wanted to lock up a berth in the knockout round without needing to earn a point on Thursday against a potent German squad.
Portuguese forward Nani opened the scoring early, in just the fifth minute, taking a lazy clearance attempt by Geoff Cameron and slamming it home over U.S. goalie Tim Howard.
"It was unbelievable," U.S. fan Carl Hren of Raleigh, N.C. told Fox News Latino outside of the stadium in Manaus. "We should have won that game. We did everything we were supposed to and we should have won."
Both sides generated a number of opportunities. One of the clearest was wasted by Michael Bradley, who had a mostly open net on a rebound, but kicked the ball straight into Portuguese defender Ricardo Costa’s left thigh.
In the 64th minute, however, Jermaine Jones sent a beautiful curling kick into the corner of the Portuguese goal. Keeper Beto was screened by other players and never even made a move to stop the ball.
About 17 minutes later, a few seconds of frenzied action led to Clint Dempsey using his chest to guide the ball into the Portuguese goal, his 39th career international goal for the U.S. Men’s National Team.
The tie leaves the U.S. tied with Germany with 4 points, though in second place based on goal differential. The Americans now need at least a tie against Germany in order to guarantee their spot in the Round of 16.
"It you would have told me before the World Cup that we would be in this position, I would have taken it in a heart beat," Hren, an 'American Outlaw' told FNL. "I think they are doing phenomenal... I just had the most fun I've ever had in 10 years tonight."
The situation is more desperate for Portugal. Tied with Ghana with one point, they need to beat the African squad by a lot of goals, and they need the U.S.-Germany game to not end in a tie.
"If we are going to become a soccer power, play with the big boys, we are going to need to know how to close games," disappointed American fan Brad Cannon of Newark, Del. told FNL after the match. "Going from the high of saying 'we are going through' to like then having to get a result against Germany - it's tough to take."