Urban drainage infrastructures are facing critical challenges due to a lack of integrated asset management, periodic maintenance, improper design, and construction methodologies. The objective of this study is to understand the urban drainage challenges and assess the failure causes and their impacts to recommend possible mitigation measures. Drainage failure causes and impacts are analyzed using the analytical hierarchy process (AHP) qualitative multicriteria decision model after conducting technical group discussions, interviews, and technical field surveys. The assessment was performed by taking representative samples from both cross- and longitudinal drainage infrastructures. The AHP analysis results showed that approximately 35.5% and 28.6% of failure causes are debris and various solid wastes for cross- and longitudinal drainage structures with correlation coefficients of 0.93 and 0.95, respectively. The result showed that design and construction defects are the second major failure causes. The research results showed that urbanization has a direct relationship with major drainage failure causes, resulting from man-made debris and solid waste clogging. On the other hand, drainage failure caused by siltation, drifts, and vegetation is higher in newly developing semi-urban and agricultural areas. The number of barrels in cross-drainage structures also contribute significantly to cross-drainage failure by creating a flow barrier due to the intermediate columns. The drainage failure impact assessment result showed that both cross- and longitudinal drainage failures primarily impact road pavement following transport disruption and traffic accidents, accounting for 38.5%, 18%, and 16%, respectively. Our research recommended that the mitigation measures for drainage failure are proper asset management and maintenance, appropriate construction supervision, and awareness creation, with weights of 36.3%, 15.5%, and 15.3%, respectively. As a drainage problem mitigation measure, the longitudinal drainage analysis results showed that the provision of a combination of cross-fall slopes, gutter slopes, and local depressions at the inlets can contribute to an increase in the trapping efficiency of the drainage system by 50%, which can reduce surface flooding substantially.