England suffered the ignominy of relegation from the Nations League's top tier after a tepid defeat to Italy that raises further concern ahead of the winter World Cup.
Among the favourites to triumph in Qatar having reached the semi-finals four years ago and the Euro 2020 final, things have gone awry for Gareth Southgate's side of late.
England failed to win any of their four June fixtures and produced a meek response to their 4-0 Molineux mauling against Hungary, with Giacomo Raspadori sealing Roberto Mancini's Italy's victory on Friday night.
A fifth straight match without a win means Southgate's men have been relegated from Group A of the Nations League - a competition they finished third in three years ago - with a game to spare.
Demotion is embarrassing but the performance is arguably of more concern given it is just 59 days until their World Cup opener against Iran.
The Euro 2020 finalists had played out a forgettable goalless draw behind closed doors in June and the first half in Milan somehow managed to be even more dreary as England toiled against the absentee-hit Azzurri.
It did not get any better from the visitors' perspective as Italy, who will not be in Qatar, kept them at bay and secured victory through Raspadori's fine curling effort.
Southgate's side lacked the ruthlessness called for on the eve of a San Siro encounter that ends with more questions than answers, with just Monday's home match against Germany to come before the World Cup.