Artificial subsurface drainage systems are often used throughout the upper Midwest to remove excess precipitation and improve crop production. However, these drainage systems export nitrate-nitrogen (NO3-N) to downstream water resources. Management practices are needed to reduce this export of NO3-N with subsurface drainage water. One such practice being considered is the use of drainage water management where subsurface water is held in the soil profile during portions of the year. Previous research has shown that drainage water management has potential to reduce subsurface drainage volume but there is still a need to understand the performance of the practice and the pathways of water flow under varying conditions. The objectives of this study, therefore, were to quantify the pathways of water movement for conventional or free drainage (FD) and drainage water management (DWM) during the growing season. In this study, six non-weighing lysimeters (0.92 × 2.30 m) with a depth of 120 cm were monitored over a 3-yr period under natural and simulated rainfall conditions. The objectives were performed to measure the effects of drainage water management (DWM) on surface runoff, subsurface drainage, and crop yield. The in-season data from natural rainfall conditions showed that DWM reduced subsurface drainage by approximately 14%. The simulated rainfall data showed that DWM increased surface runoff by 54% when the water table was established at 90 cm below the soil surface, and by 87% when the water table was established at 60 cm below the soil surface. Overall DWM was found to have the potential to reduce subsurface drainage but there is the potential that at least a portion of this reduction may be reflected in an increase in surface runoff.