Vergassola learned to play football at Sarzanese, a club from the province of La Spezia. In 1992 he moved to Carrarese Calcio, for which he played in Serie C1. In 1996 Vergassola went to Liguria to Sampdoria. There, in the encounter Atalanta - Sampdoria he made his Serie A debut on March 9, 1997 ( 4-0).
The Torino 2003 soared from to Serie B and Vergassola left the club during the season towards Tuscany and signed in Siena.
Since 2004 Simone Vergassola plays for AC Siena, who established himself with him in the major league. After the 2009/10 season, however, he rose with the Tuscans from the B series. In April 2011 Vergassola extended his expiring at the end of the season contract early by the end of the season 2012/13.