In 2010, he left for Serie B club U.S. Grosseto F.C. On 31 August 2011, Grosseto announced that he was transferred to U.S. Triestina Calcio. The club was newly relegated to 2011–12 Lega Pro Prima Divisione. Triestina bankrupted and folded at the end of season, thus Allegretti became a free agent
On 30 November 2012, Allegretti was signed by another third division club Barletta.[4] He made his debut in the following match day (2 December).
Following retirement, he took on a coaching career, starting with newly-founded amateur club Città di Cologno, starting in the Terza Categoria league (at the very bottom of the Italian football pyramid), and leading them to promotion to Seconda Categoria in his first season.[6]
He successively took on at amateur Promozione club FC Primorje, winning promotion to Eccellenza in his second season.[6] In the summer of 2019, after obtaining the UEFA A coaching badges, he returned to Monza as a youth coach, first in charge of the Under-17 and then of the Under-19 Primavera squad.[6]
On 6 September 2021, he was unveiled as the new head coach of FC Chievo 2021 (then renamed FC Clivense for legal reasons),[7] a new club founded by Sergio Pellissier and admitted to Terza Categoria following the exclusion of his and Allegretti's former team A.C. ChievoVerona from Serie B.[8] In the following season, after Clivense's acquisition of Eccellenza club San Martino Speme, which led to the former occupying a slot in the fifth tier of Italian football, Allegretti was confirmed head coach, with Pablo Granoche as his assistant.[9]
In his second season in charge of Clivense, he led the Verona-based club to win the league title, thus ensuring promotion to Serie D.[10] He departed from Clivense by the end of the season, only to return in charge of the team, now called ChievoVerona, on 9 October 2024.[11]
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