 Prior to turning professional, Roloff played two seasons in the United States Hockey League (USHL) with the Green Bay Gamblers, and then played four years of college hockey at University of Vermont with the Vermont Catamounts men's ice hockey team.After he completed his collegiate career, Roloff played five games in the AHL for the Providence Bruins at the end of the 2009–10 AHL season, and the following season he was signed by the Portland Pirates to an AHL Standard Player's Contract.In 2011, Roloff opted to continue his career overseas, embarking on a three-stint with the Augsburg Panthers of the Deutsche Eishockey Liga (DEL), the highest level of professional ice hockey in Germany.