Brake pad wear forecasting, due to its complex nature, is very difficult to describe using engineering formulas. Therefore, the aim of this publication is to create high-quality brake pad wear forecasts based on three stochastic quantitative models based on multiple regression models (linear model, inverted linear model, and power model). The matrix of explanatory variables was extracted from the controllers of 29 vehicles: A—the driver’s style of using the brake pedal specified on a 4-point scale and B—the number of vehicle load ranges specified on a 5-point scale. Methodology: A matrix of explanatory variables was obtained over a 2-year period from trucks carrying oversize loads via OBD2 socket. The trucks operated under similar operating conditions. The created models were verified in terms of their fit to the source data and by analyzing the residuals of the models. It should be emphasized that only the linear model met all the required criteria. The inverted linear and power-law models were rejected. Results: The verified linear model is characterized by very small MAPE errors. The model was validated on 4 trucks and the brake pad wear prediction errors ranged from −0.39% to 7.03%.