Maspero's career came to prominence most notably with his time at then-Serie A club Cremonese, with whom he started playing professionally and played in two one-year spells in the Italian top flight. He came into his own during the promotion season of 1992–93 and impressed greatly in a side coached by Luigi Simoni which finished 10th in Serie A during the 1993–94 season. He established a reputation as a gifted playmaker.