ku dhameystir weedha soo socota: Woolley wuxuu dhigan jiray jaamacada Michigan State University ee East Lansing, MI ka hor inta aysan Washington Capitals u dooran 61aad ee guud ahaan
Ciyaaryahankii ugu horeeyay ee NHL 1989 Xilli ciyaareedkii ugu wax soo saarka badnaa ee Woolley wuxuu ahaa 1998-99 xilli ciyaareedkii uu la qaatay Buffalo Sabres kaas oo uu ku dhaliyay 10 gool iyo 33 caawin (43 dhibcood). Sanadkaas ayaa sidoo kale ahaa ciyaartii ugu fiicnayd ee Woolley ee playoff-ka (4 gool, 11 caawin, 15 dhibcood) markii Sabres uu u gudbay Finalka Stanley Cup ka hor inta uusan ku dhicin Dallas Stars lix ciyaarood. Woolley wuxuu dhaliyay gool aad u cajiib ah oo ku guuleystay ciyaarta OT ee ciyaarta 1 ee taxanahaas, oo lagu calaamadeeyay "toogashada laga maqlay adduunka hockey-ka" oo uu ku dhawaaqay afhayeenka Sabres Rick Jeanneret.