Five new species of the endemic giant pill-millipede genus Zoosphaerium from Madagascar are described: Z. muscorum sp. n., Z. bambusoides sp. n., Z. tigrioculatum sp. n., Z. darthvaderi sp. n., and Z. heleios sp. n. The first three species fit into the Z. coquerelianum species-group, where Z. tigrioculatum seems to be closely related to Z. isalo Wesener, 2009 and Z. bilobum Wesener, 2009. Z. tigrioculatum is also the giant pill-millipede species currently known from the highest elevation, up 2000 m on Mont Andringitra. Z. muscorum and Z. darthvaderi were both collected in mossy forest at over 1000 m (albeit at distant localities), obviously a previously undersampled ecosystem. Z. darthvaderi and Z. heleios both possess very unusual characters, not permitting their placement in any existing species-group, putting them in an isolated position.