Operating vehicles in adversarial environments between a recurring origin-destination pair requires new planning techniques. A two players zero-sum game is introduced. The goal of the first player is to minimize the expected casualties undergone by a convoy. The goal of the second player is to maximize this damage. The outcome of the game is obtained via a linear program that solves the corresponding minmax optimization problem over this outcome. Different environment models are defined in order to compute routing strategies over unstructured environments. To compare these methods for increasingly accurate representations of the environment, a grid-based model is chosen to represent the environment and the existence of a sufficient network size is highlighted. A global framework for the generation of realistic routing strategies between any two points is described. This framework requires a good assessment of the potential casualties at any location, therefore the most important parameters are identified. Finally the framework is tested on real world environments.