Five of the Best Goals from Napoli and AC Milan’s Epic 1987-92 Rivalry
By Emmet Gates
To fans of a certain vintage, Napoli vs AC Milan is a springboard back in time.
The teams meet at the Stadio Diego Armando Maradona on Sunday, but when the pair are mentioned together, memories flood back of the iconic rivalry in the late 1980s and early 1990s.
Back then, they were jostling for domestic supremacy in Serie A, at a time when the league was the greatest in the world, arguably the best the game has ever seen.
In one corner there was Napoli with Antonio Careca, Alemao and Maradona; in the other was Milan with the Tre Tulipani – Marco van Basten, Frank Rijkaard and Ruud Gullit.
The tussles over a five-year period from 1987 were legendary. A battle not just for sporting greatness but pride: north against south; Silvio Berlusconi’s riches against Corrado Ferlaino’s half-riches; the genius of Maradona against Van Basten’s magnificent elegance.
Many of the goals scored during those years were spectacular, and here Destination Calcio looks at some of the best.
Diego Maradona, Napoli 2-1 Milan, April 1987
Who better to start with than Diego?
Maradona could have had the whole article to himself as he seemed to save his best for the Rossoneri during this era.
He scored seven times against Milan, most of them brilliant, often the kind of goal only he could score. But in the interest of sharing the limelight, he is only allowed a single entry.
This one came in the historic title-winning campaign. The match was played at the Stadio San Paolo, as it was known then, in late April, with only four games remaining.
Napoli were already one up through an Andrea Carnevale header before Maradona reminded everyone — again — of his unparalleled genius.
Three minutes from half-time, Bruno Giordano collected the ball from Alessandro Renica down the left-hand side, 30 yards from goal.
He moved infield before looking up and spotting Maradona’s run in behind the Milan defence. The striker floated a beautiful ball over the top.
Maradona was now at nearly full pace and being tracked by Filippo Galli as the ball comes over his shoulder. His first touch was exquisite, cushioning the ball as it fell out of the Neapolitan sunshine.
Now facing the rampaging Milan goalkeeper Giulio Nuciari who had darted off his line, Maradona had to act quick and shuffle his feet at lightning speed. His second touch rounded the keeper —without the ball hitting the turf — and the third touch slotted it home.
It was technically flawless. A moment of true genius. Simply Maradonian.
The win all but secured their first ever Scudetto with only three games remaining.
One of Berlusconi’s greatest disappointments was not being able to prise Maradona from Napoli a few years later.
“A profound regret, and not only because Maradona was the greatest player of his generation,” he confessed in a 2023 interview. “He was a fragile person, perhaps the discipline and attention to individuals that existed in my Milan would have helped him avoid some mistakes.
“However, that day, talking to him, I realised one thing: Maradona was Napoli, he was the symbol and the flag of the greatest Napoli team in history.”
Marco van Basten, Napoli 2-3 Milan, May 1988
The game to end all games between these two, and one of the most iconic matches in Serie A history.
On a steaming hot Sunday in Naples, Arrigo Sacchi’s Milan knew a victory would almost certainly bring the title with it. Napoli had been favourites to win the Scudetto, but a monumental collapse in the spring had given Sacchi’s side the opportunity to lay claim to a first league trophy since the late 1970s.
A point separated the sides going into the game. The gap had been five at one time which, in the two-points-per-win era, was huge.
“I don’t want to see a single Milan flag at the San Paolo,” remarked a bullish Maradona ahead of the game. “We are at home and for them it must be like a graveyard. Here they must die. I want to see the San Paolo all blue.”
He got his wish, as the concrete bowl was awash with 82,000 people all wearing Azzurri. They witnessed a game of the highest calibre.
Sacchi’s side struck first through Pietro Paolo Virdis, an unheralded Italian striker during the period. Maradona then replied with a stunning free-kick that skimmed off the top of Gullit’s dreadlocks en route to the top corner.
Then Gullit took over. In his first season at Milan, the Dutchman won the Ballon d’Or in 1987 and while Maradona was the best player in the world, Gullit proved he was his equal on the day.
With the score 2-1 to the Rossoneri after Gullit set up Virdis for his second, he stole the show.
The Holland international was fed down the left by Paolo Maldini. He had half a pitch of free space and only two Napoli defenders in front of him.
He switched on the afterburners and skipped past Tebaldo Bigliardi with such ease that the Napoli defender might as well have not been on the pitch.
Striding into the Napoli box, Gullit looked up and slid the ball across for Van Basten, who slammed home to land the killer blow.
It was a lightning counterattack from Milan, and from Gullit. While technically gifted and tactically astute to play in multiple positions, here he looked a vision of the future, a player sent back in a DeLorean to show the 1980s what the game would become in 15 years.
Van Basten would score better goals against Napoli, including a poker in 1992, but this one meant the most.
Maradona and the San Paolo had been silenced. Despite Careca getting a late consolation, the title was on its way north again. Napoli’s title collapse, to this day, remains a mystery.
Yet Sacchi had his one, and only, title. And Gullit played a massive part in it.
Antonio Careca, Napoli 4-1 Milan, November 1988
Is there a more underrated Brazilian striker than Careca?
Overlooked by modern audiences in favour of Romario, Ronaldo, Rivaldo and Ronaldinho, Careca’s reputation suffers from his peak coinciding with Brazil generally being poor in the late 1980s and early 1990s.
But that shouldn’t take away from his brilliance. He stayed at Napoli for six years and scored more than 70 goals. Few of them are better than this effort.
Six months after that 3-2 defeat in the classic that secured Milan the Scudetto, Careca and Maradona were out for revenge. Milan were on the receiving end of a trashing.
Maradona, again, produced a moment of brilliance, showing how to nullify Sacchi’s revolutionary offside trap with a ludicrous 30-yard header over the keeper.
Careca then doubled the lead just before half-time with a volley, while defender Giovanni Francini added a third. Napoli left the best for last.
With just 12 minutes remaining, the Partenopei again broke Milan’s press. Antonio Carannante, a relatively unknown figure for Napoli during this era, launched the ball over the top into the surging Careca.
The Brazilian had started his run in his own half, bypassing Milan’s high line. He was in the clear but still had half of the pitch to cover.
Mauro Tassotti was in hot pursuit, but Careca charged forward, controlled the ball, kept his composure and slammed a right-foot shot into the opposite corner of Giovanni Galli’s net.
It was a magnificent finish, and it put the icing on the Neapolitan cake. The score was 4-1 and Napoli had got some measure of revenge for the previous May.
Neither would win the Scudetto that season as Inter Milan and Lothar Matthaus romped to the title. But both won European honours, with Milan lifting the European Cup while Napoli won the UEFA Cup, demonstrating just how dominant Serie A was becoming on the continent.
Paolo Maldini, Milan 3-0 Napoli, February 1990
You probably didn’t expect Maldini to be on such a list, but arguably the greatest left-back in the history of the game was also capable of scoring the odd goal or two.
After Inter strode to the title previous year, Milan and Napoli had reasserted themselves at the Italian summit and were now in another battle for the Scudetto.
Napoli had eviscerated Milan 3-0 in Naples in October, with Maradona again in delicious form.
By the time the two met in mid-February, Napoli had lost only once, while Milan had been beaten four times and needed a win to stay in the race.
On a horrendous winter San Siro turf, the home side put Napoli to the sword. Daniele Massaro gave Milan the lead two minutes into the second half with a thumping header, before Maldini chipped in with his only goal of the season.
In the 70th minute, Milan won a free-kick on the right-hand side of the Napoli box. Alberico Evani stood over the ball with the intent of swinging it in with his left foot.
The likes of Van Basten, Rijkaard and Massaro were the main targets in the box. Yet no one clocked Maldini.
As the cross floated over, Maldini, who was on the edge of the box, made a surging run to meet it and leapt to power a stunning header past Giuliano Giuliani to double his side’s advantage.
It was Maldini’s first goal in Serie A for two years, and it was one even Van Basten would have been happy to claim as his own.
Milan would complete the rout with Van Basten, not wanting to be outshone by Maldini, scoring a header of his own. Three goals, three headers, and Napoli had suffered a second defeat of the season.
Maradona, for once, had been neutralised.
Gianfranco Zola, Napoli 1-5 Milan, November 1992
Napoli were demolished by Fabio Capello’s frighteningly good Rossoneri side, with Van Basten scoring four times, but they could take at least a little comfort from delivering the goal of the game.
By this point the rivalry was as good as done. Maradona had been cast out of Serie A and Italy as persona non grata following the build-up to the semi-final of Italia 90 and a failed drug test.
With Maradona’s hasty exit, Corrado Ferlaino scaled back the club’s ambitions as debt continued to mount. Napoli went from competing for titles to scrapping for a UEFA Cup spot.
Zola had been Maradona’s understudy during those chaotic and dark final months of his time in Naples. The man himself anointed Zola as his heir once he left, and the diminutive Sardinian was doing his best to fill the mightiest of shoes.
Now the creator-in-chief for Napoli, Zola scored 13 goals in his first full season without Maradona as they finished a respectable fourth under Claudio Ranieri.
Sacchi was also now gone from the scene, having left Milan to take over Italy at the end of 1991.
Capello had replaced Sacchi, and the former Juventus midfielder had taken Milan to abnormal heights. They remained unbeaten in 1991-92, and by the time they travelled down to Naples to face their old enemy, it looked like another league title was nearly in the bag.
By the time Zola stepped up to take a free-kick in the 83rd minute, Napoli had been torn to shreds by Van Basten, who delivered a masterclass in expert finishing in what was one of his last great performances.
Stefano Eranio had added to Napoli’s misery, and as Zola stood on the edge of the box to the left-hand side, the score was 5-0.
Zola, with what was to become his trademark, bent the free-kick beautifully over the wall and into the opposite corner of Francesco Antonioli’s goal. Despite the result, it drew applause from those inside the San Paolo.
In a game best remembered for Van Basten’s brilliance, a final stand before injury cruelly curtailed one of the all-time great careers, it was Zola who produced a true moment of magic, bookending one of Serie A’s greatest rivalries.
Having been named Serie B player of the month for February following his series of sparkling displays for table-topping Sassuolo, it was a fitting reward for hotshot Armand Lauriente. With14 goals and five assists in 27 appearances this season, after scoring in Sassuolo’s 5-1 win over Reggiana on Saturday, there’s no doubting what a key
Oumar Solet stole the show in Udinese's defeat against Inter Milan, but could the Frenchman be Serie A's next great defender?
In the lead up to the titanic clash with AC Milan, three Napoli heroes were honoured by the club they starred for back in the day.