Zvonimir Boban had another gear and he used it to leave a Napoli defender in his rearview mirror. It's January 4, 1998, and Fabio Capello's ill-fated second stint in charge of Milan is enjoying a good day for a change. After cutting inside the box, Boban looks up and sees a shaven headed Leonardo, then 28 and in his first season at the club, standing alone, apparently invisible to the opposition, pointing with both hands to his feet. The pass delivered doesn't disappoint and on receipt is hit first time high into the Napoli net to open the scoring on a cold and crisp day at San Paolo.
Leonardo's goal, one of three he would score in that League campaign, is often forgotten amid the dreariness of that season. Milan finished 10th, which, though an improvement on the previous year, was rendered all the more disappointing by a galling defeat to Lazio in the Coppa Italia Final. The strike is worth remembering, if anything, because it marked the first time that Leonardo came across Max Allegri, then a new recruit at Napoli brought in by his great mentor Giovanni Galeone and now his opponent in the Derby della Madonnina on Saturday.
They shared the field at San Paolo for just over an hour and as players their paths would never cross again. Whilst Leonardo went on to win the Scudetto under Alberto Zaccheroni the following season, Allegri took a step down again and returned to Pescara in Serie B, the scene of his best years. From a professional standpoint, the setting for their next meeting would be Coverciano, the FIGC's coaching school of excellence. It was before the start of the 2008-09 season. Leonardo was still behind a desk at Milan and Allegri had got his first job in Serie A with Cagliari after leading humble Sassuolo to promotion to the second tier.
Famously, he lost his first five games at the helm of the Sardinian outfit and with Massimo Cellino, a reputed mangia-allenatori, in the boardroom, Allegri's career as a top-flight tactician had no sooner started than it looked like ending. A change in the colour of his suit and accommodation out of superstition provided a much-needed change in fortune. As fate would have it, the turning point came against Milan, a 0-0 draw at Sant'Elia saving Allegri's skin. By the end of the season, he had improbably beaten Jose Mourinho to Italy's Coach of the Year award, the Panchina d'Oro.
When Carlo Ancelotti departed for Chelsea in May 2009, Allegri was among the favourites for the job at Milan. He had even earned half-baked comparisons with Arrigo Sacchi such was his rise to prominence. But Adriano Galliani decided to go with his gut and follow another glorious precedent in the club's history, namely the 'Capello model' – that is promoting from within. Leonardo was handed the reins. And so the 4-2-Fantasia was born, an attacking style of play inspired by, but perhaps not as sophisticated as Tele Santana's 1982 Brazil side.
The outcome, however, was the same. Milan ultimately didn't win anything, but produced a spectacular brand of football that lived long in the memory. Leonardo's two encounters with Allegri's Cagliari are offered up as the epitome of his philosophy. In the first game at San Siro, Milan went ahead after six minutes, only to concede an equaliser shortly afterwards and then fall behind. Marco Borriello restored parity and Alexandre Pato put Milan in the lead again all in the space of 45 minutes. Ronaldinho added to their advantage from the penalty spot after the break but Nene set up a nervy finish by pulling one back for the visitors.
The match ended 4-3 in Milan's favour prompting La Gazzetta dello Sport to suggest: "They should distribute a pill for their supporters' coronaries." Their advice was valid at Sant'Elia too last April with five goals coming in the first half alone. Leonardo was victorious again on that occasion to the tune of a 3-2 scoreline. He'll perhaps be aware that that triumph also fell on the same weekend as the upcoming Madonnina exactly a year ago.
Though few Milan derbies have had as much title deciding potential as Saturday's, one that immediately springs to mind happened on March 28, 1965. Helenio Herrera's Inter were seven points behind their rivals in January and no one gave his side a prayer, not in the age of two points for a win. But on the eve of the Madonnina, the gap had closed. Inter had given themselves a chance. They were now three points behind Nils Liedholm's Milan and knew that although a victory wouldn't result in first place, it would be psychologically crushing to the League leaders as the end of the season approached.
Stunningly Inter won 5-2 with goals from Jair, Angelo Domenghini, Mario Corso and a brace from Sandro Mazzola. Their performance is remembered as the Derby of the Century. Milan collapsed. The Scudetto was lost and Inter were triumphant. The parallels are thought provoking. History arguably stands on Leonardo's side this weekend and although that in itself doesn't guarantee a result, his past record with Allegri does give cause for the neutrals to rejoice, as it guarantees goals, and not just one or two, but plenty of them.