The paper presents the results of investigations performed in the peripheral milling of oak wood (Quercus robur), where the impact of cutting regime elements and tool geometry on the cutting force is analyzed. A large-scale experiment was conducted to implement the obtained results in developing a reliable analytical and simulation model for analyzing and predicting the cutting forces, depending on the feed rate, the milling depth and the tool rake angle. The generated mathematical model is adequate and describes accurately enough the dependence of the cutting forces upon the selected impact factors in the adopted test conditions. The evaluation of the model parameters significance indicates a significant impact of feed rate and milling depth, whereas tool rake angle does not show any significant impact in this case. The developed mathematical model can be employed in manufacturing conditions as an indicator of wood and wood-based materials machinability.