A Hundred Years Between Fog and Fire
Milan keeps its age the way it keeps its recipes — this is a city that stirs saffron into rice and calls the result gold, so alchemy has never frightened it — and in 1999 the red-and-black half of the city turned one hundred. The arithmetic was English, as the founders were: in December 1899 a band of expatriates led by Herbert Kilpin gave the town a Milan Foot-Ball and Cricket Club, with Alfred Edwards installed as its first president, and while the cricket withered politely, the football spread like vine through every courtyard from the Navigli to the shadow of the Madonnina. The club lights its candles on 16 December, though the original charter was lost somewhere in the intervening century and the historians — a tribe that has never met a certainty it could not complicate — suspect the true signing came a few days later, most likely the 18th. No matter. A hundred years is a hundred years whichever evening you choose to raise the glass, and the calendar of 1999 belonged to the Diavolo from its first Sunday to its last.
The Italy around the birthday cake was itself changing currency, literally. On the first day of January the euro entered the ledgers as an accounting currency, the lira beginning its long goodbye even though the notes and coins would wait until 2002; Massimo D'Alema's centre-left governed in Rome while Milan's own president, Silvio Berlusconi, led the opposition from the benches of Forza Italia, his Fininvest and Mediaset empire making him at once the most powerful and the most divisive of Italians; and from March to June the country found itself drawn into NATO's air war over Kosovo, aircraft lifting from Italian bases toward the Balkans. Against such weather — political, monetary, martial — a football centenary might seem a small thing. Milan has never believed that, and 1999 would give the anniversary a crown no committee could have commissioned.

The San Siro museum's display case headed CENTENARIO DEL MILAN 1899-1999: Paolo Maldini's shirt, labelled by the curators "maglia centenario Milan 1999/00", hung beside the signed centenary board. Note the breast — no club badge, but the white shield and red cross of the city of Milan itself, worn for the hundredth year. The club had turned a hundred on 16 December 1999, six months after the captain lifted the sixteenth scudetto.
Vasil Evlogiev (UserBG), via Wikimedia Commons — CC BY-SA 4.0
Zac, Whom Nobody Had Invited
The champion of the centenary was built by a man the prophets had overlooked. Alberto Zaccheroni arrived from Udinese carrying a heresy in his suitcase — a 3-4-3, later refined into a 3-4-1-2, in a country that had spent decades perfecting the art of the locked door — and carrying, too, two of his Udinese instruments: Oliver Bierhoff, the German who ruled the air as if he held its title deeds, and Thomas Helveg, the Dane who worked the flank like a courier with a train to catch. To these were added the Argentine Roberto Ayala at the back and Jens Lehmann between the posts — though the German, squeezed out of the gloves after five league appearances, would be back home at Borussia Dortmund before the new year had properly begun — while above them all sat the familiar hierarchy — Berlusconi as president and owner, Adriano Galliani running the shop as vice-president, and Paolo Maldini wearing the armband as though he had been born with the crease already pressed into his sleeve. Zaccheroni, whom we may call Zac because the season made the abbreviation affectionate, noticed that not one newspaper had listed Milan among the favourites, and he made sure his players noticed it too; there is no yeast like being left off the guest list.
The cup soon confirmed the prophets in their scepticism. Torino were dispatched in the round of thirty-two, but then Lazio put Milan out of the Coppa Italia in the round of sixteen — 3-1 at the Olimpico on 29 October 1998, then 1-1 at San Siro on 11 November, a 4-2 aggregate that closed one road and left only the long one, the league, the road that crosses the whole winter. In hindsight the pruning helped: a tree with one branch feeds all its sap to that branch.
Seven Sundays of Sap Rising
For most of the campaign the title looked bound for Lazio. The Romans led the table for long stretches and scored sixty-five league goals while doing it, playing the sort of spring-water football that seduces neutrals; but the league is a moralist and keeps its accounts to the last page, and on the penultimate Saturday, 15 May, away at the Franchi, Lazio left a fatal point on the table in a 1-1 draw with Fiorentina — Batistuta ahead inside a quarter of an hour, the equaliser arriving but nothing more — the kind of small wound that does not bleed until later. The same weekend Milan beat Empoli and went top, with one Sunday left to hold it. Milan, meanwhile, had stopped drawing and stopped losing altogether: seven victories in a row to close the season, seven Sundays of sap rising through the old trunk, until the arithmetic that had seemed decorative in March became a guillotine in May.
Zac's champions won it with figures a bookkeeper would admire sooner than a poet: twenty wins, ten draws, four defeats, seventy points; fifty-nine goals scored and only thirty-four allowed. Bierhoff finished with twenty in the league, third in the capocannoniere accounts behind Udinese's Márcio Amoroso on twenty-two and Fiorentina's Batistuta on twenty-one — the striker Zac had brought down from Udine proving, week after week, that a header is not a percussion instrument but a form of punctuation. Behind Milan's seventy and Lazio's sixty-nine came Fiorentina with fifty-six, Parma with fifty-five, Roma with fifty-four: a championship of one point, which is to say a championship of character.
Rain at the Renato Curi
The last day, 23 May 1999, was played in rain at Perugia, on a pitch the Stadio Renato Curi had left to soak until it resembled risotto — and for once Milan did not keep the afternoon waiting. Andrés Guglielminpietro struck after eleven minutes; Oliver Bierhoff headed the second on the half-hour, from an Albertini corner, the German settling the argument in the air as he had settled it all winter. Two goals in thirty-one minutes of mud, and the century looked ready to bow.
It was not so simple. On thirty-four minutes Hidetoshi Nakata, the Japanese playmaker who had turned that Perugia side into the neutral's favourite, pulled one back from the penalty spot, and the rest of the day became an examination of the nerves. Down at the Olimpico Lazio were doing everything that could be asked of them, beating Parma 2-1 with two goals from Marcelo Salas, so that a single Perugia equaliser would have put the title on a train heading south. It never came: Christian Abbiati, the young goalkeeper thrust into the run-in, produced the save of his life on a Bucchi header, the 2-1 held to the whistle, and the scudetto — the sixteenth in the club's history — came home to Milan by a single point, seventy against sixty-nine, in the exact season of the club's hundredth year. There are titles won by procession and titles won by comeback in the rain on the final afternoon; the centenary deserved the second kind, and the gods of the calendar, who are rarely so tidy, delivered it. Maldini lifted a scudetto the Englishmen of the lost charter could never have imagined; Berlusconi had his crown in the year of the candles; and Zac, whom nobody had invited, sat at the head of the table.

The shape itself: the 3-4-3 Alberto Zaccheroni carried down from Udinese and refused to abandon. Three at the back, four straight across, three men high — a heresy in the Italy of 1998, mocked through the autumn, and the frame on which a tenth-placed Milan built the sixteenth scudetto, settled on the final Sunday of the 1998-99 season.
Jackholmes (originally uploaded to Italian Wikipedia), via Wikimedia Commons — Public domain (PD-user — released into the public domain by the author)
The Boy Who Outran the Cloud
That summer the club went shopping for its second century and came back with a boy from a country younger than some of its defenders. Andriy Shevchenko was born on 29 September 1976 in Dvirkivshchyna, a village in what was then Soviet Ukraine, and raised in Kyiv; in the spring of 1986, nine years old, he was evacuated with his youth sports group when the Chernobyl reactor burned not far to the north — a childhood interrupted by an invisible cloud, which may explain the particular quietness he carried ever afterward. He might have been a boxer; he chose the ball instead, and at Dynamo Kyiv the old master Valeriy Lobanovskyi machined him into a European phenomenon, the hat-trick he scored at Camp Nou against Barcelona in 1997 serving as the continent's formal notification.
Milan paid a reported twenty-five million dollars in the summer of 1999 — a then-record fee — for the twenty-two-year-old, and brought in beside him a snarling young midfielder from Salernitana named Gennaro Gattuso and the Brazilian Serginho from São Paulo, while the other door swung outward: Roberto Donadoni, for whom the centenary title had been a sixth and final scudetto, left for Al-Ittihad in Saudi Arabia, and Christian Ziege for Middlesbrough. The supporters, still warm from Perugia, asked the eternal August question — what exactly have we bought? — and were answered on 28 August, the opening weekend, when the Ukrainian scored on his Serie A debut in a 2-2 draw with Lecce, as though introductions bored him.
By the following May he would hold twenty-four league goals from thirty-two matches and the capocannoniere crown, twenty-nine goals in all competitions — a foreigner topping the scoring charts of the most suspicious league on earth in his very first season, a thing almost without precedent. But the date on which Sheva stopped being a purchase and became a son of the house arrived earlier, in October, beneath the Madonnina; we will come to it.
An Autumn of Small Print
First, the small print of the champion's autumn, of which there was a great deal. On 21 August, at a San Siro only a quarter awake — 25,001 through the gates — Parma, holders of the Coppa Italia, beat the champions of Italy 2-1 in the Supercoppa Italiana, and the season's curtain-raiser fell on Milan's own stage. An omen? The autumn would argue so.
Europe, the theatre where this club has done its most celebrated acting, supplied the year's true heartache. Drawn into a first group stage with Chelsea, Hertha Berlin and Galatasaray, Milan opened with a goalless draw at Stamford Bridge on 15 September, beat Galatasaray 2-1 at San Siro on the 21st, and then began letting in points the way a tired roof lets in Lombard rain: 1-1 at home to Hertha on the 28th, beaten 1-0 in Berlin's Olympiastadion on 20 October, 1-1 with Chelsea at San Siro on the 26th, and finally, on 3 November amid the din of the Ali Sami Yen in Istanbul, a 3-2 defeat to Galatasaray. One win, three draws, two losses; six scored, seven conceded; six points — and last place in the group, beneath Chelsea's eleven, Hertha's eight, Galatasaray's seven. The champions of Italy were out of Europe before the trees were bare.
And yet the same autumn produced the year's warmest evening. On 23 October, in the Derby della Madonnina, Inter went ahead through a Ronaldo penalty after twenty minutes; then the Brazilian was sent off for a foul on Ayala, and the reply came after the interval from the new boy: Shevchenko's first derby goal, bundled in from close range off a defender's attempted clearance, the opening entry in what would grow into the fixture's all-time record of fourteen. George Weah headed the winner from a corner in the closing minute — 2-1 to Milan — and the curva understood — as the curva always understands before the press does — that the twenty-five million dollars had been not a price but a dowry.
The league season those months had opened would end, the following spring, in third place: sixty-one points from sixteen wins, thirteen draws and five defeats, sixty-five scored against a telling forty conceded — a Milan still handsome going forward and no longer to be trusted behind, the champions descending into the merely good. Weah himself went on loan to Chelsea on 11 January 2000, the Ballon d'Or of 1995 slipping out through a side door while the Ukrainian who had inherited the curva's affection marched on toward twenty-four league goals and the capocannoniere. The drop from the centenary summit framed the seasons that followed — the interregnum before Carlo Ancelotti took the bench in 2001 and a new Milan was set to simmer. But that is another chapter's broth.
The Hundredth December
And so to 16 December 1999, the day the club long ago chose for its birthday, one hundred years after the Englishmen of the Foot-Ball and Cricket Club put their names to a paper the century then misplaced. A centenary is a mirror: Milan looked into it and saw, within a single twelvemonth, everything it has ever been — champion by one point in the rain of May, mortal in the group stage by November; the old guard captained by Maldini, the new century announced by a quiet Ukrainian with a boxer's discipline and a sniper's calm. The verdict on 1999 is easily written and hard to better: the club marked its hundredth year in the only way that would not have been an anticlimax, with the scudetto, its sixteenth, and then spent the autumn being reminded that immortality is granted to clubs and never to seasons. The candles went out; the fog came down over the city the way it always does; and somewhere beyond the Madonnina, though nobody could yet prove it, the second hundred years had already begun to score.

The trophy hall at Casa Milan: an outsized European Cup engraved with the club's winning years, ringed by lit niches holding a century of silver. This was the inheritance Milan carried into its centenary — and in May 1999 the sixteenth Italian title was added to it, the first since 1996 and the answer to three seasons of humiliation.
UserBG, via Wikimedia Commons — CC0 1.0 Universal Public Domain Dedication
Sources
- 1.AC Milan official — the 1998-99 centenary scudetto and the final day at Perugia
- 2.Wikipedia, 1998-99 AC Milan season — Zaccheroni, signings, record, Coppa Italia exit
- 3.Wikipedia, 1998-99 Serie A — final table, one-point margin, capocannoniere standings
- 4.Wikipedia, 1999-2000 AC Milan season — Supercoppa, Champions League group stage, third place
- 5.Wikipedia, Andriy Shevchenko — biography, record transfer, debut, capocannoniere, derby record
- 6.MilanPress — 23 October 1999 derby, Shevchenko's first derby goal
- 7.Wikipedia, AC Milan — 1899 foundation, Kilpin and Edwards, disputed charter date
- 8.Transfermarkt — Perugia 1-2 Milan, 23 May 1999 match sheet (scorers, line-ups)
- 9.Wikipedia, 1998-99 Coppa Italia — Milan's round-of-32 and round-of-16 ties
- 10.RSSSF — Hertha BSC in the 1999-2000 Champions League, first group stage dates and scores
- 11.LazioWiki — Fiorentina-Lazio 1-1, 15 May 1999, the penultimate-day slip