Born in Massa but hailing from nearby Carrara, Baldini started his coaching career in 1984 at the age of 26 with Bagnone, an amateur Seconda Categoria team, which he led to immediate promotion in his debut year.
In 1997, Baldini was chosen to fill the Chievo Verona head coaching position on what was his first Serie B job, leading the gialloblu to a final seventh place in the league table.
Assigned to guide the Rosanero to immediate promotion to Serie A, Baldini was given a squad including star players such as Luca Toni or Gianluca Berti (which he brought with him from his experience at Empoli).
In January 2004, following a 1–3 home defeat to Salernitana, Baldini criticized his chairman Zamparini for his words regarding the team's recent performances; he was subsequently fired, leaving Palermo in third place, and replaced by Francesco Guidolin who eventually guided the Sicilians to win the league title.
[3] Baldini returned to coach in the 2004–05 season with Parma, being appointed in September to replace Cesare Prandelli; however, he was sacked himself in December 2004, leaving his side in second-last place in the Serie A table.
However, a row of poor results quickly pushed Catania down to 18th place, being potentially relegated as of Week 31, and with only three points ahead of last-placed Empoli, persuading Baldini to resign from his post on 31 March 2008.
He was, however, dismissed from his coaching post after failing to guide Empoli back to the top flight, following an unimpressive fifth place in the regular season and a successive defeat to Baldini's former club Brescia in the promotion playoff semi-finals.
[10] After almost four years in charge of Carrarese, during which he consistently led the club to reaching the promotion playoffs, most prominently being eliminated in the semifinals by Bari in the 2019–20 season, Baldini resigned on 10 April 2021, following a fifth consecutive defeat in the Serie C league at the hands of AlbinoLeffe.
[12] Under his tenure, Baldini successfully turned the club's fortunes, also becoming a fan favourite due to his temper and his attitude toward the city, as well as changing the playing style into a more attacking one, making room for players such as Matteo Brunori (who eventually ended up becoming the top goalscorer in all Italian professional leagues with 29 goals) to shine.