Mexico face a real battle to qualify for the last 16 at the World Cup after being held to a goalless draw by ten-man Angola.

Ricardo La Volpe's men had plenty of possession but lacked the cutting edge necessary to break down the massed ranks of the Angola defence.

Rafael Marquez hit the post with a free-kick in the first half, while Omar Bravo struck the woodwork late on when he looked odds on to score.

Angola deserved their late stroke of luck after stifling the attacking efforts of a team ranked in the top ten in the world, while occasionally threatening on the counter.

Mexico may now have to win their final Group D game against Portugal to be certain of progressing, while Angola are still in with a chance of going through if they can beat Iran.

La Volpe's men started well and Carlos Salcido was inches away from breaking the deadlock in the first minute with a dipping shot which eventually landed on top of the net.

Thirteen minutes later Marquez powered a free-kick through the wall, only to see the ball rebound to safety off the post.

Angola goalkeeper Joao Ricardo was beaten by both efforts, but improved as the game went on and produced some vital blocks late on.

As the game approached half-time the Africans, prompted by the influential Paulo Figueiredo, started to get on top and won a succession of corners. However, the delivery was consistently poor and they were unable to test Oswaldo Sanchez.

Mexico came out stronger after the break and Marquez fashioned an early chance for Guillermo Franco. The Villarreal star didn't react quickly enough and allowed Manuel Loco to beat him to the cross.

Franco's lethargy was a symptom of Mexico's unimaginative approach and as the second half progressed they struggled to create genuine scoring opportunities.

Andre Macanga then gave Angola real problems by picking up a second yellow card for a needless handball in midfield.

Almost immediately Jesus Arellano created a golden opportunity for Mexico to take the lead, but fellow substitute Jose Francisco Fonseca failed to make clean contact with the ball and his volley dribbled wide.

Another substitute, Ramon Morales, crossed for Bravo to head wide, before Joao Ricardo produced a magnificent save to keep out Marquez's long-range effort.

Joao Ricardo then flapped at the resulting corner, gifting a chance to Bravo two yards out. The striker wasn't good enough to tuck the ball away from an acute angle and instead saw it hit the outside of the post and rebound to safety.

As the ball dribbled away, so did Mexico's chance to book their place in the last 16 with a game to spare.