Giacomo Raspadori's goal was enough to see Italy beat England 1-0, confirming the visitors' relegation to group B of the Nations League on Friday night.
A dull first half saw both teams struggle to truly take a hold of the game, with an obvious lack of quality in possession hampering both sides.
England failed to pick up after the break despite a few bright moments from individuals when the game stretched. Roberto Mancini's side looked refreshed after making substitutions and drew ahead after 68 minutes, piling the pressure on the visitors to respond and stealing the win on an otherwise dull evening of football.
Italy initially got the upper hand by pressing high and catching England on the ball early on, but the first quarter of the game was a nervy affair. Neither side was able to sustain possession or build any genuine threat, with possession turning over quickly but no clear cut chances emerging.
Phil Foden looked brightest for England when dropping deep for the ball and creating space for a midfielder to run in behind. While he wasn't always found, his movement caused problems for the hosts and gave both Reece James and Jude Bellingham the space to move forward into.
Wide areas were where Italy could hurt England. Federico Dimarco always found the room for a deep cross to the back post, while Bukayo Saka looked uncomfortable at left wing-back throughout the majority of the first half, whenever the hosts attacked down his flank.
But while each side found an avenue to get forward on occasion, the game lacked any real quality and both goalkeepers remained largely untested, as the game trundled into half-time at 0-0.
The game stretched somewhat after the break and England had rare moments of joy when the likes of Bellingham, Foden and Raheem Sterling had the space to run past defenders on the counter attack. A combination of lacking quality and lacking numbers in attacking support rendered their efforts useless, though.
Dimarco found a way beyond England's back line just before the hour mark and squared the ball to Nicolo Barella who, on the stretch, sliced the ball wide. The play was flagged for offside after, but it was a let-off for Gareth Southgate's side.
England seemed to lose their tempo beyond the hour mark and substitutes added another layer of quality for Italy, who took the lead after 68 minutes. Giacomo Raspadori plucked a long ball out of the air and, in a matter of a few touches, found space to wrap a low shot beyond Nick Pope for 1-0.
Truthfully, despite a few promising individual performances, England never looked like scoring an equaliser and a change of system late on just opened up more chances for the hosts, who eased to victory in Milan.
Italy vs England: Player ratings - UEFA Nations League
1. Italy (3-5-2)
GK: Gianluigi Donnarumma - 6/10 - Yep, he was there. That's about it.
CB: Rafael Toloi - 5/10 - Asserted himself physically on both Kane and Sterling. Wasn't tested all that much, though.
CB: Leonardo Bonucci - 7/10 - Showed his age whenever England tried to counter attack, but also showed his class with some shrewd blocks as the game grew on. Classy outing.
CB: Francesco Acerbi - 6/10 - Had a cross nabbed off him early on in the second half that would've been a real chance at goal.
RWB: Giovanni Di Lorenzo - 6/10 - Probably should've capitalised on Saka looking so vulnerable on the same flank.
CM: Nicolo Barella - 5/10 - Threatened a few times when getting on the ball higher up the field, but simply didn't see enough of it. Should've scored from Dimarco's square ball after an hour, offside or not.
CM: Jorginho - 6/10 - Kept things ticking over nicely, as Jorginho does. In every game ever.
CM: Bryan Cristante - 5/10 - The game passed him by somewhat.
LWB: Federico Dimarco - 7/10 - Plenty of space to whip in a cross in wide areas. Took him a while to find his range, but, eventually, did exactly that. Problem causer.
ST: Giacomo Raspadori - 7/10 - Quiet all game, but came to life when it mattered. Beautiful first touch, even better finish.
ST: Gianluca Scamacca - 6/10 - Glimpses of his quality were on show with sharp touches and physical showings, but he was marked out of the game by two central defenders for the most part.
SUB: Wilfried Gnonto (63' for Scamacca) - 6/10
SUB: Tommaso Pobega (63' for Barella) - N/A
SUB: Manolo Gabbiadini (81' for Raspadori) - N/A
SUB: Emerson (88' for Jorginho) - N/A
SUB: Davide Frattesi (88' for Dimarco) - N/A
2. England (3-4-3)
GK: Nick Pope - 6/10 - Very, very little he could do to stop the opener for Italy. Quiet other than that beyond a few claims and kicks.
CB: Kyle Walker - 4/10 - Stood off Raspadori and gave him far too much room to fire at goal. Shouldn't have even let him take it out of the air in the first place.
CB: Eric Dier - 5/10 - Defensively sound on his return to the setup, but lacked the belief to properly step out with the ball. Didn't do enough to help out Walker to deal with Raspadori later on.
CB: Harry Maguire - 5/10 - No catastrophes. Suppose that's what happens when you put pace around him - and play him in a team that is endlessly defensive.
RWB: Reece James - 4/10 - Surprisingly wasteful in possession; particularly in wide areas,
CM: Jude Bellingham - 7/10 - Looked lively when exchanging quick passes with Foden and bursting forward into space. At his best when given licence to bring the ball forward.
CM: Declan Rice - 5/10 - Could've been braver and got himself on the ball more often. Too safe on an evening that needed more risks.
LWB: Bukayo Saka - 5/10 - Lost at sea in a position that does very little in getting the best out of him.
RW: Phil Foden - 7/10 - Caused Italy problems when dropping deep and playing passes around the corner. Creative spark.
ST: Harry Kane - 6/10 - Starved of service for the most part in a frustrating evening for strikers.
LW: Raheem Sterling - 6/10 - Marked out of the game completely, but was bright on the rare occasion he could burst forward with the ball.
SUB: Jack Grealish (72' for Saka) - N/A
SUB: Luke Shaw (72' for Walker) - N/A