Brentford's hopes of qualifying for the Milk Cup Finals lie in the balance after a 2-1 defeat against Benfica at Rugby Avenue.
Enrique Pina Calero and José Gomes scored either side of Seth Owens' dismissal for violent conduct to put Benfica firmly in control.
However, despite being down to ten men The Bees kept pushing for the draw that would secure qualification and reduced the arrears in the closing stages as Bradley Clayton scored his third goal in three games.
The Bees could not find the equaliser and frustrations boiled over at the final whistle with Jordan Carey seeing red for dissent.
The result means that Brentford need CSKA Moscow to lose by two or more goals to Manchester United tonight to have any hopes of making the top four.
After a cagey opening quarter of an hour the Portuguese side took the lead as Calero got in behind The Bees defence and slotted home from the edge of the box.
As the game developed it was clear to see that Brentford were playing all the football while Benfica were looking to work the channels at every opportunity.
Courtney Senior shot over from 20 yards before Owens forced a good low save from Fábio Miguel Silva Duarte.
From the resulting corner Owens should have levelled things but he shot over from 6 yards.
Reece Cole forced Duarte into a smart save before Gomes should have put the Portuguese side two to the good on the stroke of half-time but he found only side netting after rounding Carey.
Brentford had started to take control of the game in the closing stages of the first-half and that trend continued in the second period.
Audrius Laucys forced a flying save out of Duarte from a free-kick and Clayton called the Benfica keeper into more action moments later.
However just as The Bees were beginning to take control they were reduced to ten-men as Owens lashed out at Enrique Pina Calero and his dramatics ensured that the referee reached for the red card.
Owens' dismissal changed the mood of the game and Benfica began to pile forward knowing a three goal win would move them above The Bees in the league table.
Calero shot straight at Carey and Chris Mepham made a brave block to deny Ricardo Jorge Silva Araujo from the edge of the box.
Eventually a second did arrive and it was a fine move which saw Araujo deliver a pinpoint cross on the run which was planted home at close range by Gomes.
At 2-0 ahead Benfica sensed blood but the young Brentford side dug in and began to claw their way back into the game.
Clayton headed straight at Duarte and Cole curled one over the bar as they finished strongly.
Cole then did put the ball in the net only to be pulled up for a debatable offside flag
However, a potentially crucial goal did arrive in injury-time as Danny Parish burst clear and although his effort was blocked by Duarte Clayton was on hand to hook home.
That was not the end of the action as Brentford goalkeeper Carey saw red after full-time for dissent meaning The Bees will be without both he and Owens for tomorrow's game.
: Jordan Carey; Seth Owens, Audrius Laucys, Chris Mepham (sub George Harmes sub 60 mins), Tom Field; Courtney Senior, Jeremiah Kamanzi (sub Dylan Hamilton-Burke 64 mins), Reece Cole, Herson Rodrigues-Alves (sub Seika Jatta 50 mins); Bradley Clayton, Courtney Austin (sub Danny Parish 35 mins)
: Cameron Greaves, Robert Mensah, James Ferry
: Seth Owens 50, Jordan Carey 70
: Bradley Clayton 70+2mins