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On 9 October 2019, Pioli was appointed as the new coach of Milan. He signed for two years.

On 6 June 2017, Pioli was named new head coach of Fiorentina. He signed for two years with another optional year. On 9 April 2019, Pioli resigned as manager.

On 3 April 2016, Pioli was sacked after a 4–1 home defeat to city rivals Roma.

On 8 November 2016, Pioli was appointed as the new head coach of Internazionale on an 18-month contract. On 20 November, Inter drew 2-2 against Milan in a Serie A Derby della Madonnina match, Pioli's first competitive match as head coach of the club. He was sacked on 9 May 2017. Inter had won 12 of the first 16 Serie A matches that Pioli was in charge of (draw with Milan, losses to Napoli, Juventus and Roma), but this was followed by two draws and five losses in their last seven Serie A matches prior to his sacking.

On 12 June 2014, it was confirmed Pioli's appointment as new head coach of Lazio in place of Edoardo Reja. In his first season at the club, he led Lazio to a third-place Serie A finish. On 11 June 2015, he was offered a new 2-year contract with an additional year option.

Pioli usually uses a 4–2–3–1 formation, or a 3–5–2 formation, with full-backs or wing-backs who actively take part in the team's attacking plays. During his time at Lazio, he often used a 4–3–3 formation. Due to his passion for basketball, he attempted to bring strategic elements of the sport into his own tactical approach as a football manager.

As a head coach of A.C. Milan, Pioli made use of an archaic WM formation, also known as 3–2–2–3. Although presented officially as a 4–3–3, the formation featured the left full-back in a more advanced position, whereas the right full-back's attacking presence was significantly limited. Another key feature of this formation was in the center, where two pairs of holding and attacking midfielders formed a square, supporting each other offensively and defensively.

On 2 June 2011, Pioli was named head coach of Serie A club Palermo, but he was relieved of his duties just 90 days later.

On 4 October 2011, Pioli was named new head coach of Bologna in Serie A, replacing the sacked Pierpaolo Bisoli. After two troublesome seasons with Bologna, both ended with the team struggling in the bottom half of the Serie A table but always escaping relegation, he was removed from his managerial duties on 8 January 2014, with Davide Ballardini appointed as his replacement.

On 10 June 2010, Pioli was named head coach of Serie A club Chievo on a 12-month contract.

In 2006, Pioli was named as Parma's head coach, therefore returning to his home city and marking his Serie A debut as a manager. However, he was sacked on 12 February 2007 after a 3–0 loss to Roma which brought Parma down to second-last place and replaced by Claudio Ranieri.

On 11 September 2007, Pioli was unveiled as new head coach of Serie B club Grosseto, replacing Giorgio Roselli, who was sacked after three consecutive defeats in the first three league matches, and managed to lead the Tuscan minnows to an impressive mid-table finish in their first season in the Serie B. He then served as head coach of Piacenza for their 2008–09 Serie B campaign. In July 2009, he left Piacenza to join Sassuolo as new head coach of the neroverdi.

From 1999 to 2002 Pioli coached Bologna's youth team (winning a championship with Allievi Nazionali's team), and Chievo's in 2002–03. In 2003–04, he was appointed as head coach of Serie B club Salernitana. He moved to Modena, still of Serie B, in 2004.

Pioli, a native of Parma, started his own playing career for his home city team, Parma. Successively, he was signed by Juventus, with whom he made his Serie A debut in 1984, winning the league title, the European Cup, the European Super Cup and the Intercontinental Cup during his three seasons with the club. After being sold to Hellas Verona in 1987, Pioli moved to Fiorentina in 1989, where he spent six years of his career, before spending two seasons with Padova. After successive season-long spells in Serie C with Pistoiese and Fiorenzuola, he ended his career in 1999 with Colorno of Eccellenza Emilia-Romagna (the sixth-highest level of Italian football at that time; the top level of the Emilia-Romagna regional league system), playing alongside his brother Leonardo.

Stefano Pioli (born 20 October 1965) is an Italian football manager and a former footballer who played as a defender. He is the head coach at Serie A club A.C. Milan.