| Stanley Cup Winner | Answer | Captain |
| Edmonton Oilers 1990 | |
| Pittsburgh Penguins 1991 | |
| Pittsburgh Penguins 1992 | |
| Montreal Canadiens 1993 | |
| New York Rangers 1994 | |
| New Jersey Devils 1995 | |
| Colorado Avalanche 1996 | |
| Detroit Red Wings 1997 | |
| Detroit Red Wings 1998 | |
| Dallas Stars 1999 | |
| New Jersey Devils 2000 | |
| | Stanley Cup Winner | Answer | Captain |
| Colorado Avalanche 2001 | |
| Detroit Red Wings 2002 | |
| New Jersey Devils 2003 | |
| Tampa Bay Lightning 2004 | |
| Carolina Hurricanes 2006 | |
| Anaheim Ducks 2007 | |
| Detroit Red Wings 2008 | |
| Pittsburgh Penguins 2009 | |
| Chicago Blackhawks 2010 | |
| Boston Bruins 2011 | |
|