Referee Mike Dean showed his 100th red card as 10-man Manchester United lost 2-1 at Wolves in the Premier League.
Ashley Young was sent off as Manchester United's Champions League qualification hopes were dented by a 2-1 Premier League defeat at Wolves on Tuesday.
United would have moved up to third in the table, ahead of Arsenal and Tottenham, with victory at Molineux but Nuno Espirito Santo's side came from behind to win thanks to a Chris Smalling own goal.
Scott McTominay's first Manchester United goal put his side ahead but Diogo Jota, who scored as Wolves knocked Ole Gunnar Solskjaer's men out of the FA Cup last month, levelled.
Young's dismissal, the 100th of Mike Dean's Premier League career, came for a foul on Jota and in the 77th minute Smalling bundled the ball into his own net to ensure United have now lost three of their last four matches in all competitions.