Despite its importance for aquatic ecosystem function and watershed carbon budgets, little is known about how land use influences dissolved organic matter (DOM) export. We investigated the influence of subsurface soil drainage, widespread in the Midwestern United States, on DOM export from agricultural fields designed to drain water at either 13 mm d-1 (conventional) or 51 mm d-1 (intense). Intense drainage exported 55% (22%) more dissolved organic carbon (DOC) per year than conventional drainage due to both increased concentration and water yield. DOC export from plots was strongly dependent on precipitation and showed considerable interannual variability. Mean DOC concentrations in drainage water were low (1.62 and 1.87 mg L-1 for conventional and intense treatments), and fluorescence index (FI) measurements showed that it had a microbial source with little evidence of terrestrially derived material, suggesting that flow through deeper, organic-poor soil horizons is important in regulating DOC export from these plots. We compared DOM in subsurface drains with downstream ditch and stream sites. Increases in DOC concentration and molecular weight accompanied by decreasing FI values at downstream sites showed that streams gain a large amount of terrestrially derived DOM during base flow transport through agricultural landscapes, probably from riparian zones. These results show that DOM compositional characteristics change with catchment area and that the relevant observation scale for DOM dynamics is likely to vary among watersheds. This study also demonstrates that land management practices can directly affect DOC via changes to water flow paths. These results are critical for improving model estimates of DOM export from agricultural landscapes as well as predicting how DOC export will respond to changing land use and climate.