Artificial subsurface drainage provides an avenue for the rapid transfer of phosphorus (P) from agricultural fields to surface waters. This is of particular interest in eastern Wisconsin, where there is a concentrated population of dairy farms and high clay content soils prone to macropore development. Through collaboration with private landowners, surface and tile drainage was measured and analyzed for dissolved reactive P (DRP) and total P (TP) losses at four field sites in eastern Wisconsin between 2005 and 2009. These sites, which received frequent manure applications, represent a range of crop management practices which include: two chisel plowed corn fields (CP1, CP2), a no-till corn–soybean field (NT), and a grazed pasture (GP). Subsurface drainage was the dominant pathway of water loss at each site accounting for 66–96% of total water discharge. Average annual flow-weighted (FW) TP concentrations were 0.88, 0.57, 0.21, and 1.32 mg L⁻¹ for sites CP1, CP2, NT, and GP, respectively. Low TP concentrations at the NT site were due to tile drain interception of groundwater flow where large volumes of tile drainage water diluted the FW-TP concentrations. Subsurface pathways contributed between 17% and 41% of the TP loss across sites. On a drainage event basis, total drainage explained between 36% and 72% of the event DRP loads across CP1, CP2, and GP; there was no relationship between event drainflow and event DRP load at the NT site. Manure applications did not consistently increase P concentrations in drainflow, but annual FW-P concentrations were greater in years receiving manure applications compared to years without manure application. Based on these field measures, P losses from tile drainage must be integrated into field level P budgets and P loss calculations on heavily manured soils, while also acknowledging the unique drainage patterns observed in eastern Wisconsin.