Maini began his career with Italian club Roma, where he won the Coppa Italia in 1991, later being loaned out to Lecce and Ascoli.
He later also played for Vicenza, Milan, Bologna, Parma, Ancona, and Arezzo, before ending his career with Fabriano.
[2][3] Whilst at Vicenza he won his second Coppa Italia title in 1997, scoring a goal in the 2nd leg of the final against Napoli.
He spent a year at the club and scored once; his goal coming in a Coppa Italia tie against Sampdoria, as Milan went on to reach the final, only to be defeated by Lazio.
[2][3] Maini was named in Italy's squad for the 1997 Tournoi de France under manager Cesare Maldini.