Cika wannan jumla: A cikin kaka na 1999, Olsen ya sanya hannu kan kwangilar shekaru biyu tare da Danish Football Association (DBU) don gudanar da tawagar 'yan wasan Denmark, mai tasiri bayan halartar Denmark a gasar zakarun Turai ta 2000. A watan Yulin 2000, ya maye gurbin kocin Sweden Bo Johansson a matsayin kocin kungiyar kwallon kafa ta Denmark. A matsayin mataimakin kocinsa, Olsen ya zaɓi Michael Laudrup. Duo din ya jagoranci Denmark zuwa cancanta don gasar cin kofin duniya ta FIFA ta 2002, wani kamfen da ya ƙare a wasan zagaye na 16 da Ingila a cikin rashin nasara 0<unk>3 bayan Denmark ta lashe rukunin rukuni na farko. Kafin gasar cin kofin duniya ta 2002, Olsen ya sanya hannu kan sabon kwangila na shekaru hudu har zuwa Yuni 2006. Lokacin da Laudrup ya ci gaba da horar da Brøndby IF, Olsen ya zaɓi Keld Bordinggaard a matsayin sabon mataimakin kocinsa. Tare da Bordinggaard, Olsen ya jagoranci Denmark zuwa
Gasar zakarun Turai ta 2004, wacce ta sake ƙare a matakin farko na bugun jini. Olsen ya kasa cancantar Denmark don gasar cin kofin duniya ta 2006, amma ya tsawaita kwantiraginsa tare da DBU a watan Nuwamba 2005. Wani ɓangare na sabon yarjejeniyar, wanda ya gudana har zuwa kuma ya haɗa da gasar cin kofin duniya ta FIFA ta 2010, shi ne ƙarin alhakin bayyana "ja thread", ko na kowa mai suna, a cikin aikin gwaninta na ƙungiyar matasa na Danish, don haka ya ba Olsen babban tasiri a kan ƙwallon ƙafa na gaba da Denmark ke takawa.