[2] He began his career with Atalanta, and later he became a pillar of the powerhouse AC Milan team of the late 1980s and early 1990s, achieving domestic and international success during his time with the club.

With Italy, he reached the semi-finals of Euro 1988, and won bronze and silver medals at the 1990 and 1994 World Cups respectively, earning 63 caps and scoring five goals over a decade.

He was later appointed head coach of the Italy national team, succeeding Marcello Lippi, who resigned after having won the 2006 World Cup.

[3][4] Donadoni was knocked unconscious and suffered a broken jaw after a violent tackle from Goran Vasilijević in the 1988–89 European Cup campaign in a match against Red Star Belgrade.

[4] Donadoni briefly rejoined Milan after the 1997 MLS season, helping lead them to another Coppa Italia final in 1998 during Fabio Capello's second spell with the club.

He soon became a key member of his national side, reaching the semi-finals of Euro 1988, and he subsequently played in the 1990 FIFA World Cup, on home soil, helping Italy to a third place finish.

He was an important member of his club and national sides throughout his career, standing out for his explosive pace, agility, dribbling skills, and technical ability; he often beat players with feints both in one on one situations, or when undertaking individual runs.

Particularly in his later career he operated in a more creative midfield role as a playmaker, due to his ability to orchestrate attacking moves for his team with his vision and passing.

On 16 August, Donadoni made his Italy head coaching debut in a friendly match against Croatia played at Stadio Armando Picchi, Livorno, which did not feature any of the 23 world champions, save for third goalkeeper Marco Amelia, and ended in a 2–0 defeat.

However, despite all the critics, Donadoni led Italy to five consecutive wins to Georgia (3–1), Ukraine (2–0) and Scotland (2–0), the former being controversial for his omission of star Alessandro Del Piero from the squad.

[28] One of the main criticisms addressed by the media towards Donadoni was his alleged lack of pressure in persuading Francesco Totti to play again for the Azzurri.

On 9 June 2008, Donadoni was handed the biggest defeat for Italy's national team in over 25 years by former Milan teammate Marco van Basten, a 3–0 loss to the Netherlands.

[30] Italy captain Fabio Cannavaro was unable to play due to injury,[31] and Donadoni was widely criticised for his choice of players for the match.

[34][35] After Italy's disappointing performance at the tournament, on 26 June 2008 Donadoni was sacked by the Italian Football Federation (FIGC),[36] which named Lippi as his replacement.

[37] On 10 March 2009, Napoli announced it had appointed Donadoni as its new head coach following the termination of Edoardo Reja after five years leading the club.

However, on 12 August 2011, two weeks prior to the start of the 2011–12 Serie A, Donadoni was surprisingly sacked by Cagliari chairman Massimo Cellino.

[42] Italian press sources cited divergencies between Donadoni and Cellino regarding the sale of Alessandro Matri to Juventus and the affair involving David Suazo, who first joined the pre-season training camp only to be asked to leave days later.

Donadoni's initial contract ran until 2013, but this was extended by two years in October 2012, the longest deal club president Tommaso Ghirardi had made with a head coach.

[45] In 2014, Donadoni guided Parma to sixth place in Serie A, helping the club to qualify for the UEFA Europa League for the first time since 2007.

However, their entry to the tournament was barred because of the late payment of income tax on salaries, failing to qualify for a UEFA license, for which the club would also be docked seven points during the 2014–15 Serie A season.