Paul Scholes was sent off as Manchester United's hopes of lifting the Super Cup ended in a 2-1 defeat by Zenit St Petersburg in Monaco on Friday night.
The former England midfielder's rash action in the final moments of the match in Monaco saw him dismissed by referee Claus Bo Larsen.
Scholes, who had been booked earlier, got a second yellow for a deliberate handball in the area with United looking to draw level.
Pavel Pogrebnyak opened the scoring and Danny, who cost an astonishing £24million, extended their lead before Nemanja Vidic pulled a goal back.
While there will be bigger prizes to win and more competitive games, it is clear the Champions League holders are thin on numbers in attack.
Cristiano Ronaldo helped lighten their load in spectacular fashion last season with 42 goals.
But he is currently sidelined through injury and United, not surprisingly miss his cunning and eye for goal.
Dimitar Berbatov could be the missing link as Wayne Rooney and Carlos Tevez worked hard but could not break down the Russian side, who sealed a memorable victory.
Sir Alex Ferguson had spoken on the eve of the match of his admiration for managerial counterpart Dick Advocaat - and United found themselves chasing the game.
Former Rangers boss Advocaat has won widespread acclaim for the way he has transformed Zenit and turned them into winners.
The Russians chalked up a notable double last season securing the UEFA Cup and their domestic title.
It was obvious from the start their confidence was high and they took the game to United.
With Owen Hargreaves and Michael Carrick both sidelined, Anderson and Nani were given added responsibility in midfield.
However, they struggled to make an impact and Nani in particular looked rusty after suspension.
United were anxious to make up for the disappointment of losing to Lazio the last time they appeared in the Super Cup nine years ago.
However Pogrebnyak was quickly into the action and peeled away from his marker before spooning his effort over the top.
United responded and Tevez sent a shot into the body of Vyacheslav Maleev after 19 minutes.
Zenit carried a threat for set-pieces, though, and a superb free kick from Alejandro Dominguez went narrowly wide of the post five minutes later .
Rooney almost put United ahead in the 35th minute after a surging run by Tevez only for the goalkeeper to make a marvellous block.
Zenit hit back immediately and Ivica Krizanac came close after another good free kick from Dominguez.
Danny then headed wide in the 42nd minute before Pogrebnyak made the breakthrough. He headed in at the back post after Igor Denisov had flicked on a corner from Dominguez to leave United rattled.
The unsettled Andrei Arshavin, who has been linked with a move to Tottenham, came on for Zenit at the start of the second half but Rooney gave them a scare in the 56th minute, getting clear on the edge of area only to see his effort go narrowly wide of the post.
Tempers flared a minute later when Vidic and Pogrebnyak were left on the floor in a nasty clash of heads.
Anderson, in particular took exception to the challenge and was booked for his troubles.
Zenit stunned United again in the 60th minute by extending their lead with a magnificent effort from Danny.
He ran from deep, shrugged off Rio Ferdinand and cut inside before rifling a shot beyond Edwin Van der Sar.
United were stung but pulled a goal back in the 73rd minute when Vidic scored from close range after Tevez had cut the ball back from the by line.
Substitute John O'Shea almost pulled United level in the 86th minute, only to see his header tipped away by the goalkeeper.
Zenit then launched a swift counter attack and Danny chipped Van der Sar but his effort went over the bar.
United's irritation at playing second fiddle to Zenit was emphasised at the death with Scholes dismissed and he will now be suspended for the home Champions League game against Villarreal.
