The level of temperature of ICE pistons is a factor that greatly affects their reliability. Therefore, the need to simulate the temperature state of pistons with sufficient accuracy and minimal allocation of resources and time exists in research and during design. Primary approaches for determining the boundary conditions of the problem of thermal conduction of the piston on the basis of criterion equations, high-level mathematical models, and empirical models are considered. The latter ones have become widespread by virtue of simplicity and ease of use in practice; their usability is limited to a certain set of operating modes of one engine or a few ones of a similar design. On the basis of data from four series of experimental tests for a well-studied diesel engine 4ChN12/14 the existing empirical models of boundary conditions, suitable for identifying the temperature state of the piston only within the respective separate series separately, are refined in the paper. Processing of the data set on the measured temperatures in the control zones of the piston was performed, and linear function approximations were found that satisfactorily describe the effect of diesel power on the specified temperatures. The model of boundary conditions for a set of eighteen separate regions on the surfaces of the piston was proposed, which takes into account the dependence of the piston temperature state on the brake power of the ICE, the crank angle of the start of fuel injection, and the conditions of cooling the piston with oil. The influence of the heat insulation layer on the piston crown surface on the heat transfer was accounted for by introducing an additional thermal resistance term into the boundary condition equations. The model made obtaining the temperature field of the piston possible in simulation that is consistent with the results of all series of experiments in the control zones of the piston periphery, the edge of the combustion chamber, the vicinity of the groove of the first piston ring, the cooled surface opposite to the combustion chamber, and the piston skirt. The importance of a gradual change in the temperature of the oil and coolant during the transition of the internal combustion engine from one mode of operation to another regarding the temperature state of the piston is demonstrated. Taking the temperatures of oil from previous modes of operation into account is recommended during the analysis of engine transient processes.