The Red Wings game on Feb. 2, 1954 was notable for two major distinctions: It was the Wing's first outdoor game, and it was against a team of inmates at Marquette State prison.
The unlikely match happened when the Wings' general manager Jack Adams and team captain Ted Lindsay visited the maximum security prison as part of a sponsored trip. That's when former Purple Gang ringleaders Harry Keywell and Ray Bernstein approached Adams and asked if they would bring the Wings up for a scrimmage, to which Adams surprisingly agreed.
An outdoor rink was made just for the occasion, and despite the fact that they were playing against a team of some of Michigan's most dangerous criminals, the Wings went ahead and clobbered the "Marquette Prison Pirates" (they stopped keeping score after the first period's 18-0). To switch things up, the Wings swapped players with the Pirates, and Gordie Howe donned a Pirates jersey.
Read more about it at the Detroit Athletic Co. blog
and the Red Wing's official site