Tripoli began his professional career in 1998 with Raleigh Flyers of the USL A-League.
[2] In 1999, Tripoli joined the newly formed Pittsburgh Riverhounds of the USL A-League.
He would play for the club for five seasons, until the September 12, 2003 when the organization was voluntarily relegated to the USL Pro Soccer League, and terminated all of its players contracts.
[3] In 2005, he signed with Windsor Border Stars of the Canadian Professional Soccer League.
In his debut season with Windsor he helped the club win the Open Canada Cup, and finished third in the Western Conference.