Argentina suffered a narrow 1-0 defeat to Portugal in an international friendly fixture, despite Lionel Messi managing to outshine his arch rival Cristiano Ronaldo at Old Trafford on Tuesday.
The friendly which was being dubbed as the ultimate showdown between Ronaldo and Messi failed to live up to its hype as both players could not quite make an impact, before being substituted at halftime.
Still, the Barcelona striker looked livelier as he struck the post and caused problems to the Portuguese defence, while his Real Madrid counterpart failed to do much as he struggled to get into the game.
However, despite Argentina clearly being the better side, it was Portugal who grabbed a last minute victory through Raphaël Guerreiro at Manchester United's home ground.
The game started with Messi setting up Angel Di Maria in the fifth minute but the out-of-form Manchester United winger dragged his effort wide of the post.
The Barcelona star himself came close to breaking the deadlock after six minutes, but his effort, following an impressive one-two with Di Maria, thundered against the post.
Portugal got their first real chance of the game at the half hour mark when Jose Bosingwa picked up Ronaldo with a long ball. The Real Madrid forward did well to control the ball, but his effort flew over the crossbar.
Messi again threatened to break the deadlock in the closing stages of the first half but the scores remained goalless as the two sides headed into the tunnel for the halftime break.
Ronaldo and Messi did not come onto the pitch, as Argentina continued to assert their dominance with Gonzalo Higuain, Di Maria and Nicolas Gaitan all threatening to break the deadlock.
The best chance of the second half arrived at the hour mark when a quick freekick resulted in Argentina driving forward through Ansaldi, who sent a brilliant low cross that just narrowly evaded Carlos Tevez's head.
More chances followed for Argentina in the closing stages of the game but they were still unable to break the deadlock.
Finally just when a goalless draw was looking inevitable, Portugal went and grabbed the winner in the first minute of injury time through Guerreiro, who powered a header home after connecting with an excellent cross from Ricardo Quaresma.
Meanwhile, a late goal from Toni Kroos helped world champions Germany record a narrow 1-0 win over defending European title holders Spain.
Germany, who already have a lot of players on the sidelines, were dealt another blow as Thomas Muller was forced off the pitch after colliding with Sergio Ramos midway through the first half.
However before leaving the pitch, Muller created an excellent chance for Germany as he sent a nice cross towards Mario Gotze, who tested Iker Casillas with a volleyed effort.
Celta Vigo striker Nolitowas was the best player for Spain as he proved to be a menace for the German goalkeeper Ron-Robert Zieler on a number of occasions.
Meanwhile, debutant Kiko Casilla, who came in as a substitute for Casillas in the 77th minute, nearly made a hash of his debut in the closing stages as he almost spilt a long-range strike from Kevin Volland.
However, the Espanyol goalkeeper could only stand and watch as Toni Kross grabbed the winner in the 89th minute of the game. The Real Madrid midfielder, after receiving a good pass from Max Kruse, slotted the ball into the bottom corner.
Elsewhere, a brace from Wayne Rooney coupled with a strike from Alex Oxlade-Chamberlain proved too much for Scotland as they succumbed to a 3-1 defeat against England at Celtic Park.
Other results: Japan 2-1 Australia, Thailand 2-0 New Zealand, China 0-0 Honduras, Slovakia 2-1 Finland, Slovenia 0-1 Colombia, Belarus 3-2 Mexico, Greece 0-2 Serbia, Austria 1-2 Brazil, Romania 2-0 Denmark, Hungary 1-2 Russia, Italy 1-0 Albania, Republic of Ireland 4-1 United States, Poland 2-2 Switzerland, France 1-0 Sweden, Chile 1-2 Uruguay, Panama 0-0 Canada, Peru 2-1 Paraguay.