Kammala jumla mai zuwa: Ba kamar a cikin horo na bazara na 2007 ba, Rollins "bai ba da tabbacin shiga kakar wasa mai zuwa ba, amma hakan ba yana nufin Phillies ba su da tabbaci" shiga kakar 2008 ba, duk da sayen Mets na Johan Santana da kuma "2007 Rollins-esque" tabbacin lashe rabon daga Carlos Beltrán. Bayan fara kakar wasa ta hanyar buga wasan gida a ranar farko, Rollins ya sauka a jerin nakasassu (DL) a karon farko a cikin aikinsa a farkon watan Afrilu, yana fama da rauni a idon sawunsa. Ya dawo a watan Mayu, kuma yana da bazara "mai amfani", a ƙarshe ya buga mafi girman aiki 47 da aka sata, duk da cewa matsakaicin batinsa ya sauka zuwa.277, kuma gidansa da RBI duka sun sauka zuwa 11 da 59 bi da bi. A cikin postseason, Rollins ya kasance babban mahimmancin ƙungiyar, wanda a ƙarshe ya lashe gasar cin kofin duniya ta 2008; a cikin jerin rukuni (NLDS), ya buga wasan gida a wasa na huɗu, kuma a cikin
ya buga wasan farko a wasa na biyar, kuma duk da gwagwarmaya a farkon Wasannin Duniya, a ƙarshe ya ba da gudummawa tare da buga yanayi mai ƙarfi, yana taimaka wa Phillies lashe jerin a wasanni biyar. A ƙarshen kakar wasa, Rollins ya sami girmamawa tare da Kyautar Littafi Mai Tsarki na Fielding don ƙwarewar kariya a matsayin babban ɗan gajeren lokaci na MLB a cikin shekara.