This article explores decision analysis regarding Drop and Hook (D&H) transportation operations at sugarcane mills. By means of a case study, a combination of a discrete event simulation model and multi-attribute utility theory was used to evaluate different configurations for sugarcane delivery systems using internal, external, or no D&H systems. A D&H strategy maximises truck utilisation, as semi-trailers can be handled independently of the traction unit of the trucks, which makes the transport system more agile. For internal D&H systems the semi-trailer detaching/attaching point is located inside the mill site while for external D&H systems it is located outside, before the trucks' weighbridge. Each configuration requires different infrastructure which affects the supply of sugarcane for milling. The case study was applied to a sugarcane mill of a corporation located in São Paulo State. By means of discrete simulation, we determined that eighteen D&H configurations were feasible. By using the swing weighting multi-criteria decision analysis (MCDA) method, we identified fleet cost as the most important factor, while configurations with external D&H systems showed the best utility values. For this case study, the best configuration is to use the external D&H strategy with 28 road trains (truck and two semi-trailers), 12 additional semi-trailer sets, and 6 tractor units.