Rubuta ci gaba don wannan sakin layi - Woolley ya halarci Jami'ar Jihar Michigan a Gabas Lansing, MI kafin Washington Capitals ta zaba shi na 61 a cikin 1989 NHL Draft
Ka yi haƙuri. Lokacin da Woolley ya fi samun nasara a NHL shi ne lokacinsa na 1998-99 tare da Buffalo Sabres wanda ya ci kwallaye 10 da taimako 33 (maki 43). Ya dace, wannan shekarar ita ce mafi kyawun wasan kwaikwayo na Woolley (4 kwallaye, 11 taimaka, maki 15) yayin da Sabres ɗinsa suka ci gaba zuwa wasan karshe na Stanley Cup kafin su faɗi ga Dallas Stars a wasanni shida. Woolley ya zira kwallaye na wasan OT mai ban mamaki a wasan 1 na wannan jerin, wanda aka lakafta shi a matsayin "harbi da aka ji a kusa da duniyar hockey" ta mai ba da labari na Sabres Rick Jeanneret.