He played in the National Hockey League for the Washington Capitals, Florida Panthers, Pittsburgh Penguins, Buffalo Sabres, and Detroit Red Wings.

[2] 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.

During Woolley's tenure with the Red Wings, they would play Sam the Sham & the Pharaoh's Woolly Bully when he scored at Joe Louis Arena.

[3] 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.