Massimo Ambrosini is a former Italian professional footballer, who mainly played as a defensive midfielder. At club level, he is mostly known for his successful time at Italian team A.C. Milan, where he spent eighteen years of his career, winning several titles, and even captained the side from 2009 to 2013, following the retirement of Paolo Maldini. A physically strong, tenacious, energetic, and hardworking box-to-box, central, or defensive midfielder, with a wide range of skills, Ambrosini was well regarded for his ability in the air, and was capable of being a goal-threat, in particular from set-pieces, due to his height, elevation, ability to make attacking runs into the area, and his heading accuracy, as well as his powerful striking ability from distance, which even led manager Carlo Ancelotti to deploy him as a centre forward on occasion. Throughout his career, he stood out for his leadership, as well as his stamina, versatility, tactical intelligence, and aggressive tackling. Although Ambrosini primarily served as a ball winner, he was also known for his ability to start attacking plays after winning back possession, courtesy of his vision and passing range, despite his lack of notable technical skills. Despite his ability as a midfielder, he often struggled with injuries throughout his career.
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The Scudetto badge is back on 1999-2000 Milan’s shirts due the 1998-1999 Serie A’s victory. The team did not repeat its successful season in 1998–99, and fell back to third in Serie A, as well as crashing out of the Champions League, following a lackluster performance in the First Group Phase. In fact, Milan ended up last in the group, and was not even qualifying for the remainder of the UEFA Cup. 1999-2000 was also Andriy Shevchenko’s first season with Milan A.C., and managed to become top scorer already in his debut season. The Ukrainian further enhanced his reputation as a fearsome striker, which was fortunate for Milan, considering Oliver Bierhoff’s scoring tally’s decline. The team showed signs of being over the hill, having had several aging players while it won the league in 1998–99.