This paper compares two metaheuristic approaches in solving a constrained transportation scheduling problem, which can be found in transporting goods in emergency situations. We compared Greedy Search, Parameterless Evolutionary Search and Ant-Stigmergy Algorithm. The transportation scheduling/allocation problem is NP-hard, and is applicable to different real-life situations with high frequency of loading and unloading operations; like in depots, warehouses and ports. To evaluate the efficiency of the presented approaches, they were tested with four tasks based on realistic data. Each task was evaluated using group and free transportation approach. The experiments proved that all tested algorithms are viable option in solving such scheduling problems, however some performing better than others on some tasks.