Originally drafted 11th overall in 1989 out of the Western Hockey League (WHL) by the Detroit Red Wings, Sillinger began his NHL career in Detroit before continuing on to play for the Mighty Ducks of Anaheim, Vancouver Canucks, Philadelphia Flyers, Tampa Bay Lightning, Florida Panthers, Ottawa Senators, Columbus Blue Jackets, Phoenix Coyotes, St. Louis Blues, Nashville Predators and New York Islanders. Of these 12 teams, Sillinger has played full seasons with only Detroit, Vancouver, Columbus and New York. During his tenure with Detroit, he captured a Calder Cup championship in 1992 with the Adirondack Red Wings, while leading the playoffs in scoring as an American Hockey League (AHL) rookie.