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Roberto Donadoni was born September 9, 1963 in Cisano Bergamasco, a small town outside of Bergamo. He was a cornerstone of the powerhouse AC Milan teams of the late 1980s and early 1990s and one of the pioneers of Major League Soccer, where he played two seasons for the MetroStars.

Donadoni started his career with his hometown team, Atalanta, in 1982. He transferred to Milan in 1986 and became a mainstay in the team. Usually playing a left midfield role, Donadoni was a vital fixture in a team that won five Serie A titles, three European Cups, three European Super Cups, and 2 Toyota Cups. A member of the Italian national team, he played in the 1990 and 1994 World Cups, helping Italy to third and second place finishes respectively. In the 1990 World Cup, he was one of the unlucky Italians that missed a penalty against Argentina in the semi-finals. Italy were eliminated, and Donadoni never took another penalty in his career.

The MetroStars of MLS made him a centerpiece of their franchise when they signed him in 1996. While with the Metros, he was recalled to the Italian national team and was widely considered their best player at Euro 96, at the age of 32. He came back to MLS, but in the league's first two formative years, Donadoni's class was often wasted. He still proved a spectacular performer, being named to the league Best XI in 1996. Unfortunately, Donadoni's genius could not bring the MetroStars any success.

Berlusconi described Donadoni as a player that could "light up any stadium". He went back to AC Milan after the 1997 MLS season, and promptly helped them to another Serie A title, his sixth. He ended his career by playing two games with Al Ittihad of Saudi Arabia.

Never a big scorer, Donadoni scored just 21 goals for Milan and 6 for the MetroStars. He added 5 for Italy in 63 caps. After retiring as a player, he coached Livorno(while in Serie B) and Genoa. He returned to Livorno and was very successful in helping them avoid relegation. The next season he was even more impressive, with Livorno sitting in the European places. He then resigned midseason because Livorno patron Aldo Spinelli blasted him in the media. After Marcello Lippi's resignation as Azzurri boss, he was hired by the FIGC to be the new head coach.