In industrial sites, the movement and contact behaviors of workers are random, but their frequency and statistical characteristics can be determined. Particularly in machining workshops, metalworking fluids (MWFs) cause liquid oil contamination on the processed workpieces, and the contamination spreads to the entire workshop given the random contact of workers or the handling of workpieces. This study proposes a contact transmission model based on the Markov chain to quantify oil contamination transfer. First, the transfer efficiency between the glove and the workpiece, which is regarded as a key model parameter in this research, was determined through experiments. The model was used to characterize and predict the spread of oil contamination across different regions, including production and assembly areas. Specifically, the oil contamination concentrations on workbench surfaces in seven locations of a machining workshop in Shanghai GKN HUAYU Driveline Systems Co., Ltd. (SDS) were measured on-site. Findings showed that the model could feasibly depict the transfer process of oil contamination across different surfaces. Then, the variation law of oil contamination concentration on the workbench surfaces over time was analyzed, the oil contamination distribution map of the entire workshop plane was drawn, and the effectiveness of two cleaning measures to reduce oil contamination concentrations was compared. The proposed contact transmission model offers a basis for identifying highly polluted surfaces in machining workshops and controlling the spread of liquid oil contamination.