Monaco and Benfica played out a goalless Champions League Group C draw at the Stade Louis II on Wednesday.
Both sides wasted clear-cut chances early in the first half before Benfica defender Lisandro Lopez was sent off 15 minutes from time for a dangerous tackle on Joao Moutinho.
Despite their numerical advantage, Monaco could not find the breakthrough in the closing stages and Benfica held on for a point.
Monaco had several chances to open the scoring in the early exchanges.
Lucas Ocampos really should have done better in the fifth minute when Dimitar Berbatov's pass found him unmarked inside the penalty area but the striker missed the target from close range with the goal at his mercy.
Benfica soon settled into the game and winger Eduardo Salvio did well to find some space at the far post, but he could not force Monaco goalkeeper Danijel Subasic to make a save as his half volley sailed high and wide.
Monaco were dealt a blow just after the half-hour mark when Berbatov, who was an injury doubt before the game, was forced off with a groin injury and was replaced by exciting young prospect Anthony Martial.
Subasic had to be alert to deny Rodrigo Lima from close range in the 39th minute but the action petered out and neither side could break the deadlock before the interval.
Benfica started the second half strongly and after a Talisca free-kick missed its target by a matter of inches, Lima almost got on the end of a probing Nicolas Gaitan cross from the left wing.
Monaco head coach Leonardo Jardim responded by introducing Yannick Carrasco in place of Ocampos but still Benfica were in the ascendancy.
Enzo Perez should have done better when he shot from the edge of the area but his effort sailed well over the crossbar.
At the other end, Geoffrey Kondogbia headed narrowly wide from a Carrasco corner before Gaitan's ambitious volley from an acute angle failed to trouble Subasic.
Benfica were reduced to 10 men in the 75th minute when Lopez was shown a red card for a late, lunging tackle on Moutinho.
Benfica boss Jorge Jesus subsequently shored up his defence by introducing Cesar in place of the inspirational Gaitan and his introduction helped Benfica see out the remainder of the match to collect their first point of this year's Champions League competition.
The stalemate means Monaco remain second in the group with five points from their three matches, while Benfica remain bottom with just the one point from their three games.
The sides face one another in the reverse fixture at the Estadio da Luz on November 4.