Descriptions are provided for males of 58 philopotamid species in the Trichoptera (caddisfly) genus Chimarra Stephens. Among these are 49 new species from New Guinea (Papua New Guinea and the Indonesian province of Papua/West Papua, including nearby islands): 41 new species from Papua New Guinea, seven from West Papua and one found in both (C. bifida sp. nov.). The new species are: Chimarra absida sp. nov., C. aliceae sp. nov., C. antap sp. nov., C. bicornis sp. nov., C. bicuspidus sp. nov., C. bifida sp. nov., C. bintang sp. nov., C. cavata sp. nov., C. clava sp. nov., C. cristata sp. nov., C. damma sp. nov., C. denticulata sp. nov., C. ediana sp. nov., C. erecta sp. nov., C. espelandae sp. nov., C. harpes sp. nov., C. huonana sp. nov., C. ismayi sp. nov., C. jari sp. nov., C. johansoni sp. nov., C. karamui sp. nov., C. kebarana sp. nov., C. kewabi sp. nov., C. kuka sp. nov., C. laensis sp. nov., C. lalokiana sp. nov., C. lindyae sp. nov., C. maai sp. nov., C. mendiana sp. nov., C. milneana sp. nov., C. missim sp. nov., C. morobensis sp. nov., C. newguineana sp. nov., C. olahi sp. nov., C. pertica sp. nov., C. pindua sp. nov., C. projectura sp. nov., C. sappela sp. nov., C. sepikana sp. nov., C. simbuensis sp. nov., C. stella sp. nov., C. supia sp. nov., C. toliana sp. nov., C. trigona sp. nov., C. ukarumpana sp. nov., C. unidentata sp. nov., C. verticas sp. nov., C. wara sp. nov. and C. wauana sp. nov. Only one described species (C. cyclopica Kimmins, 1962) is shared by the two adjoining countries. Species separation is based almost entirely on male genitalic characteristics. The C. papuana species group (after Mey, 2006; Oláh, 2014) is reaffirmed; its key features being inferior appendages with the sub-terminal or terminal process elongate and an elongate ventral process on segment IX. All 58 species treated here are endemic to New Guinea, except for C. biramosa, which was originally recorded from the nearby Solomon Islands (Kimmins, 1957).