Bruno Fernandes was sent off as Manchester United crashed to an embarrassing 2-0 defeat at lowly Wolves, while Erling Haaland missed a penalty as crisis-torn Manchester City failed to end their dismal run with a 1-1 draw against Everton.
United suffered a third successive loss in all competitions to leave new boss Ruben Amorim with five defeats in his 10 games since replacing the sacked Erik ten Hag.
Fernandes was dismissed two minutes into the second half at Molineux for a second booking after fouling Nélson Semedo.
United's 10 men cracked in the 58th minute, when Matheus Cunha's corner went straight in as goalkeeper André Onana flapped under pressure from Matt Doherty and Santiago Bueno.
Hwang Hee-chan compounded Amorim's misery when he tapped in with just seconds left.
It was another bitter blow for United, who endured a humiliating 3-0 defeat by Bournemouth at Old Trafford last weekend after losing 4-3 in the League Cup at Tottenham.
With his team marooned in 14th place – just eight points above the relegation zone – Amorim's woes might not be over, with United facing in-form Newcastle on Monday before travelling to Liverpool in their first game of 2025.
"It's so tough to win games in this league with 11 men. With 10 men, it's more difficult," Amorim said. "Of course, when you lose, when we don't win, it's a step back – it was really hard with the sending off."
Wolves climbed out of the bottom three thanks to their second successive win under new manager Vitor Pereira.
Meanwhile, campions Manchester City have just one victory in their last 13 games in all competitions as their Christmas schedule started in disappointing fashion.
Bernardo Silva put City in front early on before Iliman Ndiaye salvaged a point for Everton.
Seven minutes into the second half, Haaland had the chance to end his longest goal drought at the Etihad but Jordan Pickford dived low to his right to make the save.
City are languishing in seventh place and sit five points adrift of the top four, with their astonishing decline showing no sign of ending.
"Of course we need results and we didn't get it. The team played really good again in all departments and unfortunately could not win," said City boss Pep Guardiola, whose side are at risk of failing to qualify for the Champions League for the first time in 15 years.
"We accept it," Guardiola added. "It is life. We did not expect it to not win games many times – but what do you have to do? Continue." (AFP)