The inland transportation takes a significant portion of the total cost that arises from intermodal transportation. In addition, there are many parties (shipping lines, haulage companies, customers) who share this operation as well as many restrictions that increase the complexity of this problem and make it NP-hard. Therefore, it is important to create an efficient strategy to manage this process in a way to ensure all parties are satisfied. This paper investigates the pairing of containers/orders in drayage transportation from the perspective of delivering paired containers on 40-ft truck and/or individual containers on 20-ft truck, between a single port and a list of customer locations. An assignment mixed integer linear programming model is formulated, which solves the problem of how to combine orders in delivery to save the total transportation cost when orders with both single and multiple destinations exist. In opposition to the traditional models relying on the vehicle routing problem with simultaneous pickups and deliveries and time windows formulation, this model falls into the assignment problem category which is more efficient to solve on large size instances. Another merit for the proposed model is that it can be implemented on different variants of the container drayage problem: import only, import-inland and import-inland-export. Results show that in all cases the pairing of containers yields less cost compared to the individual delivery and decreases empty tours. The proposed model can be solved to optimality efficiently (within half hour) for over 300 orders.