Transportation is a key logistics function, which determines the dynamic nature of material flows in logistics systems. At the same time, transportation is a source of uncertainty of logistics operations performance in the supply chain. Obviously, the development of a new approach for evaluation of the duration of delivery “Just-In-Time” (JIT) will improve the efficiency of supply chains in accordance with one of the major criteria, namely customer satisfaction. One of the basic approaches to make effective management decisions in transportation and other logistic operations is the JIT concept. In the majority of examined sources the JIT concept is described on the verbal level without any usage of calculation dependences. The paper is devoted to the formation of analytical and simulation models, which allow obtaining the probabilistic evaluation of the implementation of unimodal and multimodal international transportation JIT. The first model where the order of the operations implementation does not affect final result is formed on the basis of the probability theory: distribution laws composition, theorems of numerical characteristics of random variables, formula of complete probability. The second model accounts the impact of operations implementation order in transportation and their interconnection and is based on the simulation (the method of statistic experiments) and shown as a corresponding algorithm, which allows to consider different limitations (technical, organizational and so on). Considered analytical dependences give the possibility to obtain the necessary estimations of the transport operations implementation according to JIT: mean transportation time, delivery implementation probability by the set moment or the delivery time with the set probability. To carry out some comparative calculations and clarify the algorithm, two international routes have been chosen: the first one is a unimodal road transportation, the second one is a multimodal transportation (road and marine transport). All the data, which is necessary for calculation has been collected on the basis of official information (in particular, the data of tachograph, special questionnaires filled in by the drivers, the survey results of the managers). For unimodal transportations analytical dependences and modelling results give close results. For the combined multimodal transportations taking into account various limitations the preference must be given to the simulation. The modelled indexes take into consideration their intercommunication and definitely estimate the supply chains reliability, and this allows decreasing the uncertainty of the logistic system.