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.