Drewiske won a the Wisconsin Hockey Coaches Association's Player of the Year award in 2003 while playing for his hometown Hudson Raiders. Drewiske was a four-year member of the UW Badger hockey team, including being the team's captain in his senior season. He won an NCAA championship with the Badgers in 2006. Drewiske is currently a member of the Montreal Canadians, and won the Stanley Cup in 2012 with the LA Kings.