Australasia harbors very high squamate diversity and is a center of endemicity for a number of major lineages. However, despite this diversity, the diplodactyloid geckos of Australia, New Caledonia, and New Zealand (comprised of three endemic families and >200 species) are the only extant squamates with unequivocal Mesozoic origins in the region. Diplodactyloid geckos also exhibit notable phenotypic and ecological diversity, most strikingly illustrated by the functionally limbless pygopods. Here, we present the first phylogenomic analyses of the pattern and timing of diplodactyloid evolution, based on a dataset of more than 4000 ultraconserved elements (UCEs) from 180 species. These analyses fully resolve nearly all nodes, including a number of intergeneric relationships that have proven problematic in previous studies. The hypothesis that New Caledonia and New Zealand clades represent independent post-KT boundary colonization events of Tasmantis from Australian ancestors is confirmed. Phylogenetic relationships recovered here further highlight contrasting patterns of diversity, most strikingly between insular and/or morphologically highly derived clades that have diversified rapidly, as opposed to other species poor and phylogenetically divergent relictual lineages on mainland Australia. Our new timetree suggests slightly older branching times than previous analyses and does not find a mass extinction event in the early Cenozoic. Finally, our new phylogeny highlights caudal variation across the clade. Most strikingly, the distinctive leaf-tail morphology shown by one family may in fact be plesiomorphic.