The club's most recent success consists of 6 consecutive participations in Serie B between 2007 and 2013, notably reaching the play-off semifinals in 2008-09.

However, in the 2006–2007 season, under head coach Antonello Cuccureddu, who replaced Massimiliano Allegri after the ninth matchday, Grosseto finally managed to win Serie C1/A following a 1–0 away win at Padova in the final matchday with a goal by Carl Valeri, thus gaining a historical spot in the Serie B 2007-08.

The 2008–09 season started with higher expectations under new head coach Elio Gustinetti; the team started its season showing a very impressive form, but then a result crisis led Grosseto out of the promotion playoff zone, causing the dismissal of Gustinetti and his replacement with Ezio Rossi.

But on 22 August 2012, Grosseto and its president are absolved by the Court of justice, eliminating the verdict of the first instance and so readmitted to Serie B.

In November 2022, famous local entrepreneur Giovanni Lamioni bought the franchise from previous owner Salvatore Guida.

Lamioni gave the presidency role to Antonio Fiorini and called back Filippo Vetrini for the general sporting director place.

The city welcomed the negotiation very positively and regained a vanished enthusiasm for the disappointing results of the previous season.

Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply.