Harry Kane became England's all-time record goalscorer as they opened their Euro 2024 qualifying campaign with a first victory in Italy since 1961.
Declan Rice gave England an early lead when he scored from close range after Kane's shot was blocked before the captain put memories of his penalty miss against France in the World Cup quarter-final in Qatar aside with an emphatic spot-kick.
Italy, whistled off at half-time in their first international in Naples for a decade, improved as England became sloppy.
Debutant Mateo Retegui was the beneficiary of poor work from Harry Maguire, whose failed attempt to close down the danger on the edge of the box allowed the Italians to shift the ball to the 23-year-old to drill an unerring finish past Jordan Pickford after 56 minutes.
England's drop in performance was compounded by Luke Shaw's second yellow card with 10 minutes left but they hung on for a vital win.
England show two sides
England's first-half display was consummate in its control, Italy made to look decidedly average as Rice and Jude Bellingham controlled affairs and Kane made history.
The only blot was a dreadful miss by Jack Grealish that would have made it 3-0 and surely avoided the anxious second-half showing that followed.
Italy were still in the hunt, just, and after what would surely have been some choice half-time words from coach Roberto Mancini they came out fighting in the second half.
Their cause was helped by an England performance barely recognisable from the first half, the visitors conceding control as well as the goal that set up a tense finish.
Shaw's dismissal did little to help England's cause late on. The defender picked up the first of his two yellow cards in the 78th minute for time-wasting when preparing to take a throw-in and the second came just two minutes later for a mis-timed challenged on Retegui.
Italy, however, lacked the quality to make England pay the price and in the end their Euro 2024 campaign got off to the ideal start.
England now have the chance to build on these three points when they face Ukraine at Wembley on Sunday.
England win in subdued Naples
The theory was that Italy's football authorities chose the ramshackle but hugely atmospheric Stadio Diego Armando Maradona to make life uncomfortable for England.
In practice, there were empty seats inside this vast bowl and Italy's poor first half meant that it took until after the break for the home support to come to life.
It had been suggested Napoli's fans struggle to form an attachment with the Italy team and their silence throughout the first half and reaction at half time suggested they could hardly wait to get back to throwing their passion and fire behind their own team as they run away with Serie A and chase the Champions League.
The subdued mood played into England's hands, Gareth Southgate's side only making life difficult for themselves with their own indifferent showing that almost allowed Italy back in.
Player of the match
GnontoWilfried Gnonto
Italy
Squad number7Player nameGnonto
Squad number1Player nameG Donnarumma
Squad number9Player nameScamacca
Squad number19Player nameRetegui
Squad number6Player nameVerratti
Squad number20Player nameTonali
Squad number4Player nameSpinazzola
Squad number17Player namePolitano
Squad number10Player namePellegrini
Squad number3Player nameTolói
Squad number8Player nameJorginho
Squad number2Player nameDi Lorenzo
Squad number11Player nameBerardi
Squad number16Player nameCristante
Squad number18Player nameBarella
Squad number15Player nameAcerbi
Line-ups
Italy
Formation 4-3-3
1G Donnarumma
2Di Lorenzo3Tolói15Acerbi4Spinazzola
18Barella8Jorginho6Verratti
11Berardi19Retegui10Pellegrini
1G Donnarumma2Di LorenzoBooked at 52mins3Tolói15AcerbiBooked at 90mins4Spinazzola18BarellaSubstituted forCristanteat 62'minutes8JorginhoBooked at 61minsSubstituted forTonaliat 69'minutes6VerrattiSubstituted forScamaccaat 88'minutes11BerardiSubstituted forPolitanoat 62'minutes19Retegui10PellegriniSubstituted forGnontoat 69'minutesSubstitutes
5Darmian7Gnonto9Scamacca12Pessina13Emerson14Scalvini16Cristante17Politano20Tonali21Falcone22Meret23RomagnoliEngland
Formation 4-3-3
1Pickford
2Walker5Stones6Maguire3Shaw
8Phillips4Rice10Bellingham
7Saka9Kane11Grealish
1Pickford2WalkerBooked at 71mins5Stones6MaguireBooked at 57mins3ShawBooked at 80mins8Phillips4RiceBooked at 29mins10BellinghamSubstituted forGallagherat 85'minutes7SakaSubstituted forJamesat 85'minutes9Kane11GrealishSubstituted forFodenat 69'minutesSubstituted forTrippierat 81'minutesSubstitutes
12Trippier13Ramsdale14Henderson15Dier16Chilwell17James18Guéhi19Gallagher20Foden21Maddison22Forster23ToneyLive Text
Match ends, Italy 1, England 2.
Second Half ends, Italy 1, England 2.
Attempt missed. Mateo Retegui (Italy) header from the centre of the box misses to the right. Assisted by Leonardo Spinazzola with a cross.
Francesco Acerbi (Italy) is shown the yellow card for a bad foul.
Foul by Francesco Acerbi (Italy).
Harry Kane (England) wins a free kick in the defensive half.
Corner, Italy. Conceded by Kalvin Phillips.
Substitution, Italy. Gianluca Scamacca replaces Marco Verratti.
Corner, Italy. Conceded by Conor Gallagher.
Foul by Marco Verratti (Italy).
Conor Gallagher (England) wins a free kick in the defensive half.
Substitution, England. Conor Gallagher replaces Jude Bellingham.
Substitution, England. Reece James replaces Bukayo Saka.
Substitution, England. Kieran Trippier replaces Phil Foden.
Second yellow card to Luke Shaw (England) for a bad foul.
Mateo Retegui (Italy) wins a free kick in the attacking half.
Foul by Luke Shaw (England).
Luke Shaw (England) is shown the yellow card.
Foul by Wilfried Gnonto (Italy).
Bukayo Saka (England) wins a free kick in the defensive half.