Presented to Flood Master Class by Insurance Business Magazine this presentation examines quantitative risk assessment of riparian, overland and wastewater (sanitary) sewer system flooding. Analysis of City of Toronto and City of Markham historical flooding is shown to be highly correlated to design standard limitations related to the era of construction. Risks are shown to extend over a range of scales from floodplain (river) to flood drain (homes) based on detailed GIS spatial analysis. Flood risk mitigation measures are presented to achieve design standard adaptation in local areas with specific limitations.