 Rosenberg akatanga mwaka wa2008-09 zvakanaka paakarova zvibodzwa zvina uye akaisa Hugo Almeida kaviri mukukunda 9-3 pamusoro peEintracht Nordhorn mumutambo wekutanga weDFB-Pokal musi wa9 Nyamavhuvhu 2008. Mazuva manomwe gare gare, musi wa16 Nyamavhuvhu 2008, Rosenberg akarova brace paakatanga mwaka mumutambo we2x2 uchirwisa Arminia Bielefeld. Mwedzi mumwe gare gare, musi wa 20 Gunyana 2008, akarova kaviri mukukunda 5-2 pamusoro peBayern Munich, achimaka kekutanga Bremen kukurira Bayern kuAllianz Arena. Izvi zvakateverwa nekurova chinangwa chake chechipfumbamwe chemwaka, mukukunda 2-1 kurwisa Erzgebirge Aue mumutambo wechipiri weDFB-Pokal. Mushure mekutanga kwemwaka wa2008-09, Rosenberg akaramba achibatanidzwa muchikwata chekutanga kunyangwe kusvika kutsva kwaClaudio Pizarro. Pasinei nekukuvara kwemhasuru kwakagadziriswa panguva yebasa renyika yose, Rosenberg akazowedzera zvimwe zvibodzwa zviviri pakupera kwa2008, achihwina Hertha BSC neInter Milan kunyange kukunda 2-1, Werder Bremen yakabviswa muboka reboka uye yakaderedzwa kuEFA Cup. Musi wa 15 Kurume 2009, Rosenberg akarova kaviri mukukunda 40 pamusoro peVfB Stuttgart, achipedza mitambo yake gumi asina kurova chinangwa. Pasinei nokuiswa parutivi gare gare mumwaka wa2008-09, akatanga mu2009 UEFA Cup Finalvachipesana neShakhtar Donetsk uye vakatamba maminetsi makumi manomwe nemasere vasati vashandurwa, sezvo Werder Bremen yakaenderera mberi ichirasikirwa ne2 × 1 munguva yekuwedzera. Kunyange zvazvo vasina kukunda UEFA Cup, kirabhu, zvisinei, yakakunda DFB-Pokal mushure mekurova Bayer Leverkusen 10. Pakupera kwegore ra2008-09, akanga aita 47 kuonekwa achiwana 13 nguva mumakwikwi ose, achiita kuti ave wechitatu wepamusoro-soro muchengeti wechikwata, shure kwaClaudio Pizarro naDiego. Zvisinei, chinangwa chake chekugadzira chinangwa chakauya pasi pekutsoropodzwa, nekuda kwekutarisira kwekuita mumwaka miviri yekutanga kuWerder Bremen. 