Sillinger played for 12 teams and was traded nine times during his NHL career, both of which are league records (tied with Brent Ashton for the latter).

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.

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.

Upon being drafted, Sillinger returned to the Pats for two more seasons, where he posted 129- and 116-point campaigns to receive WHL Second and First All-Star Team honours in 1990 and 1991, respectively.

Due to the 1994–95 NHL lockout, Sillinger went abroad to play in the Austrian Hockey League for EC Wien, where he tallied 27 points in just 13 games.

When NHL play resumed, he appeared in 13 games for the Red Wings before being traded to the Mighty Ducks of Anaheim on April 4, 1995 with Jason York for Stu Grimson, Mark Ferner and Anaheim's 6th round choice in 1996 NHL Entry Draft (used to select Magnus Nilsson).

[1] Sillinger remained in Anaheim the next season, but was traded the following campaign in 1995–96 to the Vancouver Canucks in exchange for Roman Oksiuta on March 15, 1996.

[1] Sillinger's stint with the Flyers began promising, scoring 22 points in the 27 games to close the season following his trade, but after managing just three assists in the first 25 games in 1998–99, he was dealt away to the Tampa Bay Lightning midway through the campaign along with Chris Gratton, in exchange for Mikael Renberg and Daymond Langkow on December 12, 1998.

Becoming an unrestricted free agent in the 2006 off-season, Sillinger joined his twelfth and final NHL team, the New York Islanders, signing on July 2, 2006.

Owen played for the Regina Pat Canadians midget hockey team and was named the most valuable player at the 2015 Telus Cup.