Harry Maguire and Reece James were red-carded in England's 1-0 defeat to Denmark in the Nations League.
It was only after the final whistle blew that an unwelcome England record was set: Two players being sent off in a match for the first time.
England played for an hour with 10 men after Harry Maguire was dismissed. A first starting appearance for England had just been completed when Reece James was red carded for confronting the referee following Wednesday's 1-0 loss to Denmark.
It was a landmark night for the right reasons for Christian Eriksen, who celebrated his 100th Denmark appearance with the winning penalty.
Gareth Southgate's lineup had already been reduced to 10 men by that point after Maguire was booked twice inside 31 minutes.
“I don’t think tempers frayed," England captain Harry Kane said. "There were some decisions that didn’t quite go our way today but that’s football.
“I don’t think we have discipline issues. It was a night when we put everything on the line. I can’t fault the boys in that aspect."
The result leaves Group 2 wide open heading into the last two rounds of matches next month. England dropped from first to third place behind Denmark and Belgium, which took the lead with a 2-1 victory over Iceland.
Three days after beating Belgium — which leads the FIFA world rankings — England's good work was undone. The hosts could feel aggrieved that in a rare top-level game without VAR, Eriksen scored from a disputed penalty awarded for Kyle Walker’s challenge on Thomas Delaney.
“It was very special,” Eriksen said after netting his 34th international goal in the 35th minute at a stadium he called home for a couple of years during his Tottenham career. “It’s not as fun to play at an empty Wembley compared to a full Wembley I’m used to."
It took quick reflexes from goalkeeper Kasper Schmeichel to palm away Mason Mount's header and tip over a free kick from Reece James to prevent England leveling in the second half.
But it had started to go wrong for England and Maguire after five minutes. The defender earned his first booking for a sliding tackle on Yussuf Poulsen, but that didn't curb his recklessness.
“I think the first yellow was a challenge he didn’t need to make," Southgate said, “and that puts him on edge and the second one is an interception with his momentum taking him through.”
When his overextended left foot caught Kasper Dolberg in the 31st, Spanish referee Jesús Gil Manzano had no option but to show Maguire a second yellow card.
It's the latest setback for Maguire, who became the world's most expensive defender when he signed for Manchester United last year. He was withdrawn by Southgate for last month's three England games after he was convicted in Greece of assaulting a police officer and attempted bribery while on holiday in August. Hanging over Maguire is an appeal process against the conviction and suspended 21-month sentence.
“He is going through a period where a lot of stick is coming his way," Southgate said. “He has our full support and I know his club will be the same. We have total belief in him."
