Before cryogenic fuel depots can be fully realized, efficient methods with which to chill down the spacecraft transfer line and receiver tank are required. This paper presents numerical modeling of the chilldown of a liquid hydrogen tankto-tank propellant transfer line using the Generalized Fluid System Simulation Program. To compare with data from recently concluded turbulent liquid hydrogen chilldown experiments, seven different cases were run across a range of inlet liquid temperatures and mass flow rates. Both trickle and pulse chilldown methods were simulated. The Generalized Fluid System Simulation Program model qualitatively matches external skin-mounted temperature readings, but large differences are shown between measured and predicted internal stream temperatures. Discrepancies are attributed to the simplified model correlation used to compute two-phase flow, boiling heat transfer. Flow visualization from testing shows that the initial bottoming out of skin-mounted sensors corresponds to annular flow but that considerable time is required for the stream sensor to achieve steady state as the system moves through annular, churn, and bubbly flows. The Generalized Fluid System Simulation Program model does adequately well in tracking trends in the data, but further work is needed to refine the two-phase flow modeling to better match observed test data. Nomenclature C p = specific heat, J∕kg · K k = thermal conductivity, W∕m · K Nu = Nusselt number Pr = Prandtl number Re = Reynolds number t closed = valve-off time, s t open = valve-on time, s u = fluid velocity, m∕s x = quality Y = mass fraction μ = viscosity, Pa · s ρ = density, kg∕m 3