Due to the increase in working hours, the reliability of rubber O-ring seals used in hydraulic systems of transfer machines will change. While traditional methods can only analyze one of the material properties or seal properties, the failure of the O-ring is caused by these two factors together. In this paper, two factors are mainly analyzed: the degradation of material properties and load randomization by processing technology. Firstly, the two factors are defined in terms of material failure and seal failure, before the experimental methods of rubber materials are studied. Following this, the time-variant material properties through experiments and load distribution by monitoring the processing can be obtained. Thirdly, compressive stress and contact stress have been calculated, which was combined with the reliability model to acquire the time-variant reliability for the O-ring. Finally, the life prediction and effect of oil pressure were discussed, then compared with the actual situation. The results show a lifetime of 12 months for the O-ring calculated in this paper, and compared with the replacement records from the maintenance workshop, the result is credible.