England fell to a first home defeat in two years as out-of-sorts Harry Maguire's sending off was compounded by Denmark centurion Christian Eriksen scoring a controversially-awarded penalty.
Three days on from impressively coming back to beat Belgium to go top of their Nations League group, Gareth Southgate's side stumbled to a first defeat on home soil since September 2018.
Eriksen's penalty shortly after Maguire received two bookings in 31 wretched minutes were the key moments at an empty Wembley, where Denmark held on for a 1-0 win against visibly-frustrated England.
It was a galling end to October's triple-header, with the post-match focus sure to be on Maguire after a nightmare performance continued a testing period for the defender on and off the field.
The 27-year-old has started the campaign poorly after a truncated pre-season overshadowed by a well-documented Greek court case, with the Manchester United captain sent off for two yellow cards.
Maguire's fifth-minute challenge on Yussuf Poulsen was bad but his lunge on Kasper Dolberg was worse, with the steepness of England's uphill battle soon increasing as Eriksen scored from the spot.
Confusion reigned at the decision to award the spot-kick that the former Tottenham playmaker lashed home, with England failing with their attempts to level.
Kasper Schmeichel superbly denied Mason Mount and Conor Coady saw a last-gasp header cleared off the line as the Three Lions failed to eke out a leveller on a night when Southgate's anger was palpable.
Referee Jesus Gil Manzano even warned the England boss for one outburst and Reece James - so impressive on his full debut - appeared to be sent off after full-time.