Gentile attended college at the where he played on the soccer team from 1992 to 1995. In 1995, the Badgers won the National Collegiate Athletic Association Men"s Soccer Championship while Gentile was selected a third team All American. In 1993, he was part of the United States U-20 men"s national soccer team at the 1993 Fédération internationale de football association World Youth Championship, but he never entered a game in the tournament.
In March 1996, the Colorado Rapids selected Gentile in the first round (9th overall) of the 1996 Draft. The Rapids released Gentile during the preseason and he signed with the Milwaukee Rampage of the USISL. On July 13, 1999, the Rampage unexpectedly released Gentile along with four other players. Gentile had started five games before being benched in June.
In February 2000, Gentile was again drafted by an Master of Library Science team when the Tampa Bay Mutiny selected him in the sixth round (66th overall) in the 2000 Master of Library Science SuperDraft.
However, on February 22, 2000, the Mutiny released Gentile and he returned to the Thunder. In 2001, he signed a one year contract, with a one year option.
He played through at least the 2002 season.
In 1995, the Badgers won the National Collegiate Athletic Association Men"s Soccer Championship while Gentile was selected a third team All American. In 1997, the Rampage won the league championship. He immediately signed with the Minnesota Thunder, going on to win the 1999 league championship with his new team
He was a member of the United States U-20 men"s national soccer team at the 1993 Fédération internationale de football association World Youth Championship.
