Province of Frosinone
Born in Frosinone, Lazio region, Cipriani started his senior career at Serie D club Anagni, located in the Province of Frosinone. In 2000 the club relegated to Eccellenza Lazio. In 2000–01 season he left for fellow Eccellenza club Ferentino, which also located in the Province of Frosinone. The club won the champion of Group B and promoted. Cipriani played 21 times for Ferentino in 2001–02 Serie D. In 2002, he was signed by another Eccellenza club Veroli, another Province of Frosinone club.