Pedzisa mutsara unotevera: Woolley akapinda Michigan State University muEast Lansing, MI pamberi peWashington Capitals yakamusarudza 61st yose mu
1989 NHL Draft. Mwaka waWoolley wakabudirira kwazvo muNHL yaive mwaka wake wa1998-1999 neBuffalo Sabres maakatora zvibodzwa gumi nemakumi matatu nematatu (43 mapoinzi). Nenzira yakakodzera, gore iroro raivewo rakanakisisa raWoolley playoff performance (4 zvinangwa, 11 zvinobatsira, 15 mapoinzi) sezvo Sabres yake yakafambira mberi kuStanley Cup Finals vasati vawira kuDallas Stars mumitambo mitanhatu. Woolley akarova mutambo-kuhwina OT chinangwa mu Game 1 yeiyo nhevedzano, yakanyorwa se "kupfura kunonzwika kutenderera nyika yeHockey" naSabres muparidzi Rick Jeanneret.