Rubuta ci gaba don wannan sakin layi - A cikin kakar wasa ta gaba, Cloutier ya yi ciniki a ranar 1999 NHL Entry Draft (Yuni 26, 1999) zuwa Tampa Bay Lightning. An tura shi zuwa Tampa Bay, tare da winger Niklas Sundstrom, zaɓaɓɓen zagaye na farko (Nikita Alexeev) a 2000
da zaɓi na zagaye na uku (daga baya aka yi ciniki) a cikin 2000, don zaɓin zagaye na farko na Haske a cikin wannan shekarar (Pavel Brendl). Tare da tafiyar tsohon dan wasan farko na Tampa Bay, Bill Ranford, zuwa Detroit Red Wings da Darren Puppa yana gab da karshen aikinsa, Cloutier ya dauki matsayin farawa don sabon kulob dinsa. Lokacin farko na Cloutier a matsayin mai farawa na NHL an katse shi a lokuta da yawa tare da raunin da yawa da dakatarwa. Ya sha wahala a cikin wani mummunan rauni a farkon yakin neman zabe a ranar 18 ga Nuwamba, 1999, wanda ya tilasta shi daga wasanni biyu. A ranar 14 ga Janairu, 2000, gasar ta dakatar da shi na wasanni hudu bayan wani lamari da ya faru da Islanders gaba Tim Connolly. Bayan haɗuwa biyu, Cloutier ya bincika Connolly, sannan ya harbi kansa (kayan kwalkwali na Connolly bai lalace ba) yayin da yake kwance a kan kankara. A watan da ya biyo baya, ya sake yin amfani da shi a ranar 21 ga Fabrairu kuma ya rasa wasanni hudu. Cloutier ya rasa wasu gasa huɗu da suka fara a ranar 14 ga Maris bayan ya ji rauni a wuyansa. Raunin sa na huɗu na kakar wasa ya faru ne a ranar 28 ga Maris, lokacin da ya yi rauni a ligament na medial collateral (MCL) kuma ya rasa wasanni biyar. Ya gama kakar wasa ta 1999-2000 yana fitowa a wasanni 52 na Haske, yana yin nasara 9, 30 da 3 a matsayin ƙungiyar ta gama na biyu a ƙarshe a gasar. Ya yi rajistar 3.49 GAA da.885 ceton kashi.