Cipriani began his career in 1995 with the New Hampshire Ramblers of the USISL Pro League.
He contributed in the clubs playoff run by recording two goals in the finals against Toronto Supra.
[4] He helped the Wolves repeat their success when the club joined the Canadian Professional Soccer League by winning the CPSL Championship in the 1998, and 2001 season.
[7] He made his official debut for Hamilton on May 23, 2002 against Vaughan Shooters, and recorded two goals in a 5-1 victory.
[8] His tenure in Hamilton was short lived due to a dispute with the team owner.