In karst regions, urban flooding is exacerbated by the presence of sinkholes that flood adjacent areas when surface runoff rates exceed sinkhole drainage rates. Repeated sinkhole flooding has occurred in Cookeville, Tennessee, causing damage to both residential and commercial areas of the city. This paper documents land use change in Cookeville between 1955 and 1997 and employs the TR-55 rainfall-runoff model to estimate the effect of these changes on sinkhole flooding. Between 1955 and 1997, the percentage of commercial land in Cookeville increased five-fold, while the percentage of residential land doubled. Over the same period land area in pasture decreased by onethird. Approximately two-thirds of the natural stream channels in the city were converted to concrete-lined channels beginning in the 1980s, further increasing runoff rates to sinkholes. In addition to increasing runoff, paving and filling of many sinkhole swallets in Cookeville has probably increased the flooding threat by decreasing sinkhole drainage rates. Results from the rainfallrunoff model suggest that urbanization has caused a tripling of flood magnitudes for some sinkhole watersheds. A 1998 storm caused floodwaters in one sinkhole to rise within 3 m of a drainage divide that separates the sinkhole from a major shopping center. Greater flood heights within this sinkhole are likely to occur in the future given that the 1998 event was estimated to be only a 1-hr, 10-yr storm, and because large amounts of debris that are regularly swept into the swallet threaten to reduce sinkhole drainage rates. Results from this study highlight the need for flood mitigation strategies that regulate urban development within sinkhole watersheds, as well as limit activities that interfere with the drainage function of sinkholes.