Osiecki played 93 games in the NHL for the Calgary Flames, Ottawa Senators, Winnipeg Jets and Minnesota North Stars.

Following his retirement as a player in 1995, Osiecki spent seven seasons as the head coach and general manager of the Green Bay Gamblers of the United States Hockey League, leading the team to a Clark Cup championship in 2000.

He then spent the next six seasons as assistant coach under Mike Eaves at his alma mater, the University of Wisconsin, winning the national championship in 2006.

[1] In 2016 Osiecki was hired as an associate coach with the Wisconsin Badgers men's ice hockey team following a stint with the Rockford IceHogs.

[2] When head coach Tony Granato was fired on March 8, 2023, it was also revealed that Osiecki would not return to the Badgers for the following season, and he subsequently became a professional scout with the Pittsburgh Penguins of the National Hockey League on August 30, 2023.