Urban green space, green infrastructure, and horticultural installations are gaining recognition for their potential to foster biodiversity. Green roofs are challenging growing environments for plants, characterized by extreme substrate temperatures, high light intensity, limited moisture availability, and limited substrate depth. Plants have a variety of physiological responses to these unique conditions, but little is known about how green roof growing conditions affect ecological characteristics like plant flowering phenology. Meanwhile, studies are only just uncovering the degree to which green roofs can provide habitat and support urban pollinator biodiversity. We evaluated the flowering phenology and made in situ pollinator observations of 15 plant taxa growing both on green roof systems and at ground level in Denver, Colorado, over two growing seasons. We found that flowering phenology occurs substantially earlier on green roofs compared to ground level among the observed plant taxa and observed a greater number of pollinators on green roofs early in the season, compared to ground level, presumably due to the availability of floral resources among the observed plant taxa. We observed significantly higher substrate temperatures along with wider diurnal temperature amplitude during the growing season that may contribute to the observed phenological patterns. Divergence in flowering phenology between individual plants of the same species on green roofs and plants at ground-level may have implications for organisms that rely on floral resources in urban environments. Earlier flower initiation on green roofs may provide pollinators with unique foraging opportunities and aid targeted conservation where early-season floral resources are limited.