Carefully designed green roofs have the potential to be used as mitigation for habitats lost at ground level. The development of plant assemblages on two green roofs designed to emulate diverse brownfield habitats (brown roofs), by using recycled demolition aggregate as part of a low-fertility growth substrate, were studied over the first four years of their development. The cover-abundance of flowering plants and habitat structural components (e.g. bare ground, moss) were measured on the Domin-Krajina scale within all identified microhabitats. Drought disturbance was one of the main controlling factors on assemblage development. Annual plants were abundant and successful in the first growth season, and thereafter only re-appeared in any numbers following drought disturbances in subsequent years. Moss and Sedum acre L. increased through the study period until these plants dominated coverage. The cover-abundance of perennial wildflower species was strongly influenced by drought disturbance. The influence of drought disturbance varied between different brown roof microhabitats, with plant assemblages in coarser and less fertile microhabitats more resistant to these disturbances. Observed responses to drought were consistent with the following two hypotheses: (i) Areas of coarse substrate can act as disturbance refugia for plants during drought by helping preserve pockets of water under large clasts and within absorbent materials such as brick. (ii) The plant assemblages living in areas of more fertile substrates, which grow more luxuriantly when water availability is high, are more vulnerable to drought disturbance. Green roofs should be designed to include a range of substrate types to create several microhabitats that will collectively support more species than any single microhabitat.