This paper is mainly about the experiment research of oil monitoring for a kind of special heavy vehicle’s transmission system. The wear elements in lubrication oil of a heavy vehicle’s transmission system were analyzed by the spectroscopic analysis method, and gear’s wear status was studied. Probability density function and probability distribution function of wear information about the elements in lubricating oil were calculated by the maximum entropy theory. The running cut-off point is obtained for diagnostic criteria of the vehicle’s failure, which provided evidence for monitoring and judging the reliability of the vehicle’s wear.