Because of their ability for aerial dispersal using silk and preference for open habitats, many wolf spiders are formidable colonisers. Pioneering arachnologists were already aware of the large and colourful wolf spiders in the Madeira archipelago, currently included in the genus Hogna Simon, 1885. The origins were investigated and species boundaries of Madeiran Hogna examined by integrating target-gene and morphological information. A multi-locus phylogenetic analysis of a thorough sampling across wolf-spider diversity suggested a single origin of Madeiran endemics, albeit with low support. Divergence time estimation traced back their origin to the late Miocene, a time of major global cooling that drove the expansion of grasslands and the associated fauna. Morphological examination of types and newly collected material revealed a new species, hereby described as H. isambertoi Crespo, sp. nov. Additionally, H. blackwalli is revalidated and three new synonymies are proposed, namely H. biscoitoi Wunderlich, 1992, junior synonym of H. insularum Kulczynski, 1899, H. schmitzi Wunderlich, 1992, junior synonym of H. maderiana (Walckenaer, 1837), and Arctosa maderana Roewer, 1960 junior synonym of H. ferox (Lucas, 1838). Species delimitation analyses of mitochondrial and nuclear markers provided additional support for morphological delineations. The species pair H. insularum and H. maderiana, however, constituted an exception: the lack of exclusive haplotypes in the examined markers, along with the discovery of intermediate forms, pointed to hybridisation between these two species as reported in other congeneric species on islands. Finally, the conservation status of the species is discussed and candidates for immediate conservation efforts are identified.