Streamflow droughts are receiving increased attention worldwide due to their impact on the environment and economy. One region of concern is the Midwestern United States, whose agricultural productivity depends on subsurface pipes known as tile drains to improve trafficability and soil conditions for crop growth. Tile drains accomplish this by rapidly transporting surplus soil moisture and shallow groundwater from fields, resulting in reduced watershed storage. However, no work has previously examined the connection between tile drainage and streamflow drought. Here, we pose the question: does the extent of watershed-level tile drainage lead to an increased susceptibly and magnitude of streamflow droughts? To answer this, we use daily streamflow data for 122 watersheds throughout the Midwestern United States to quantify streamflow drought duration, frequency, and intensity. Using spatial multiple regression models, we find that agricultural tile drainage generates statistically significant (p < 0.05) increases in streamflow drought duration and intensity while significantly reducing drought frequency. The magnitude of the effect of tile drainage on streamflow drought characteristics is similar to that of water table depth and precipitation seasonality, both of which are known to influence streamflow droughts. Furthermore, projected changes in regional precipitation characteristics will likely drive the installation of additional tile drainage. We find that for each 10% increase in tile-drained watershed area, streamflow drought duration and intensity increase by 0.03 d and 12%, respectively, while frequency decreases by 0.10 events/year. Such increases in tile drainage may lead to more severe streamflow droughts and have a detrimental effect on the socio-environmental usage of streams throughout the Midwest.