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Following a torn ACL to defenseman Jiri Fischer in November of 2002, the Red Wings acquired Woolley from the Sabres for a conditional draft pick. During Woolley's tenure with the Red Wings, they would play Sam The Sham & Pharoh's Woolly Bully when he scored at Joe Louis Arena. Woolley was also a participant in the 2014 Bridgestone NHL Alumni Winter Showdown at Comerica Park on December 31, 2013, representing the Detroit Red Wings.

He played for Canada at the 1992 Winter Olympics. Woolley recorded five assists in eight games with the team, scored a shootout goal, and won a silver medal.

Woolley attended Michigan State University in East Lansing, MI before the Washington Capitals selected him 61st overall in the 1989 NHL Draft. Woolley's most productive NHL season was his 1998–99 campaign with the Buffalo Sabres in which he netted 10 goals and 33 assists (43 points). Fittingly, that year was also Woolley's finest playoff performance (4 goals, 11 assists, 15 points) as his Sabres advanced to the Stanley Cup Finals before falling to the Dallas Stars in six games. Woolley scored a dramatic game-winning OT goal in Game 1 of that series, labelled as "the shot heard round the hockey world" by Sabres announcer Rick Jeanneret.

As a youth, Woolley played in the 1981 and 1982 Quebec International Pee-Wee Hockey Tournaments with a minor ice hockey team from Mississauga.

Jason Douglas Woolley (born July 27, 1969) is a Canadian retired professional ice hockey defenceman. He played in the National Hockey League for the Washington Capitals, Florida Panthers, Pittsburgh Penguins, Buffalo Sabres, and Detroit Red Wings.