Early career 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. 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 starting three league matches, and managed to lead the Tuscan minnows to an impressive mid-table finish in their debut 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.
Chievo On 10 June 2010, Pioli was named head coach of Serie A club Chievo on a 12-month contract.
Palermo 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.
Bologna 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.
Lazio On 12 June 2014, it was confirmed Pioli's appointment as new head coach of
Lazio in place of
Edoardo Reja. In his debut 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. On 3 April 2016, Pioli was sacked after a 4–1 home defeat to
city rivals Roma.
Inter Milan On 8 November 2016, Pioli was appointed as the new head coach of
Inter Milan on an 18-month contract. On 20 November, Inter drew 2–2 against
AC 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 starting 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.
Fiorentina On 6 June 2017, Pioli was named new head coach of
Fiorentina. He signed for two years with another optional year. Pioli was in charge of the team when on 4 March 2018 central defender and captain
Davide Astori died unexpectedly; to honour the memory of the player, Pioli got a commemorative tattoo. On 9 April 2019, Pioli resigned as manager.
AC Milan 2019–2021: Early seasons The day after
Marco Giampaolo's sacking, on 9 October 2019, Pioli was appointed as the new coach of
AC Milan, on a deal to the end of the season. Pioli's Milan finished the season in sixth place in Serie A. The team scored 63 goals in the competition, their highest total since 2013. On 7 July 2020, Milan defeated Juventus 4–2. Milan scored four goals against Juventus in Serie A, last accomplished in March 1989, when the score was 4–0. Milan last defeated Juventus in 2016. On 21 July, Pioli reached an agreement with Milan to extend his contract as head coach by two years, to June 2022. On 17 October, Milan won 2–1 against Inter. Milan's last defeat of Inter in Serie A was in 2016. Milan last won four consecutive season-starters in Serie A in
1995–96, when
Fabio Capello was in charge. Milan scored in 24 consecutive Serie A games, last accomplished in 1973 (29). On 6 December Milan beat Sampdoria 2–1, setting a new club record for goals scored in successive Serie A matches (30). Following a 2–2 draw with
Genoa on 16 December, AC Milan were unbeaten in 24 league games: their longest run since 1993. On 23 December, Milan beat Lazio 3–2, becoming the second side in the history of
Europe's top five leagues to have scored two or more goals in more than 15 successive games in a single calendar year (after Barcelona, 18 in 1948). On 9 May 2021, Milan had their an away win against Juventus (3–0), last accomplished in 2011. Three days later, Pioli's side beat
Torino 7–0 in an away game, winning by a seven-goal margin, last accomplished against
Udinese (7–0) in June 1959. A 2–0 away win against
Atalanta on 23 May confirmed that Milan would finish second in the league, securing a return to the
Champions League, last accomplished seven seasons earlier. Milan also set a new all-time record for away wins in a Serie A season, with 16; no side has ever achieved more in Europe's top five leagues in a single campaign. Real Madrid in 2011–12 and Manchester City in 2017–18 also achieved 16 away wins. In the
UEFA Europa League, Milan reached the round of 16, where they were eliminated by
Manchester United.
2021–22: Scudetto victory As of August 2021, Pioli held the second highest win percentage in Serie A among Milan coaches, behind only
Lajos Czeizler. On 3 October, Milan defeated Atalanta at
Gewiss Stadium 3–2, recording successive away wins against Atalanta in Serie A, last accomplished in 2013. On 31 October, with a 2–1 win against Roma, Milan became the fourth team in Serie A history to win 10 of their 11 season starter games, after Roma, Juventus (twice) and Napoli (twice). The win also ended
José Mourinho's run of 43 home games unbeaten in Serie A. In November, Pioli reached an agreement with the club to extend his contract until June 2023. In December, his Milan side became the second team in Serie A history to win at least 17 away league games in a single calendar year (after Napoli, 18 in 2017). In the
Champions League, the team was knocked out at the group stage, finishing bottom of Group B behind
Liverpool,
Atlético Madrid and
Porto. On 6 January 2022, when Milan defeated Roma 3–1, they won three consecutive league games against Roma last done in 1996. On 5 February, Milan came back to beat archrivals Inter 2–1 in the
Derby della Madonnina after trailing by 0–1; comeback last accomplished by Milan in the derby in 2004. On 13 February after defeating
Sampdoria, Milan had picked up 55 points in the league: in the three points-per-win era, only in
2003–04 had they earned as many points after 25 games (64). On 6 March, Milan beat Napoli 1–0 at
Stadio Diego Maradona, moving to the top of the league and winning two consecutive away games against Napoli in Serie A last done in 1981. Milan had also picked up at least 60 points from the 28 season starter matchdays of Serie A last done in
2011–12. On 12 March, Milan defeated
Empoli 1–0, reaching 63 points on the top of league table. Seven days later, Milan beat Cagliari 1–0; with that win, Milan had scored at least one goal in 15 consecutive away matches in a single top-flight season for only the second time in their history, also doing so in
1967–68 in Serie A. Pioli's side sealed the
Scudetto on 22 May, the last day of the season, with a 3–0 win against
Sassuolo. It was Milan's last league title since 2011, and Pioli's first-ever trophy. The team amassed 86 points in total, their best tally since
2005–06. Pioli's tenure at Milan has brought him the praise of several Italian football personalities and pundits, such as
Alberto Zaccheroni,
Fabio Capello,
Claudio Ranieri,
Arrigo Sacchi and
Adriano Galliani.
2022–2024: Later seasons and departure in 2022 On 13 August 2022, Milan defeated
Udinese 4–2, securing three consecutive wins at the start of the
competition for the first time in 26 seasons, last accomplished in 1996. On 31 October, Milan announced that Pioli extended his contract until 30 June 2025. On 8 March 2023, Milan beat
Tottenham 1–0 on aggregate, reaching
Champions League quarter finals last done in the 2011–12 season. On 2 April, Milan squashed Napoli 4–0 at
Stadio Diego Armando Maradona, inflicting their worst defeat since 2007. With that win, Milan won three successive matches in Naples, last done in 1951. On 18 April, Milan beat Napoli 2–1 on aggregate following a 1–1 draw, reaching the Champions League semi-finals, last done in the 2006–07 season. Milan eventually lost to city rivals Inter 3–0 on aggregate in the semi-finals. On 28 May, he led Milan to qualify for the Champions League for a third successive season following a 1–0 win at Juventus. Milan started Pioli's final season with an away win against
Bologna on 21 August. On 7 October, after a difficult win against Genoa, Milan stood at the top of the league table. However, the team lost the lead in the league table after a 0–1 loss against Juventus on 22 October. Milan was knocked out of the
Champions League group stage on 13 December, finishing third in the group and qualifying to the UEFA Europa League instead. On 20 January 2024, after 3–2 win against Udinese, Pioli reached a milestone of 100 wins for Milan in the league, becoming the fifth manager to achieve the feat after
Carlo Ancelotti, Fabio Capello,
Nereo Rocco and
Nils Liedholm. On 24 May 2024, AC Milan announced that Pioli would depart after the end of the
2023–24 season.
Al Nassr On 18 September 2024,
Al Nassr announced that Pioli had signed a deal to coach the team after they dismissed
Luís Castro. On 25 June 2025, it was announced that Pioli had been released with immediate effect as manager of the club.
Return to Fiorentina On 12 July 2025, Pioli returned to Fiorentina as head coach, marking his second spell at the club. His second stint as Fiorentina manager proved to be difficult from the very beginning, with the
Viola failing to win any of the first ten league games, leading to Pioli's demise on 4 November 2025, two days after a 0–1 home loss at the hands of
Lecce left Fiorentina dead last in the table. ==Style of management==