The high temperature generated on the contact interfaces of the conical friction element in clutches due to the sliding frictional heat should be responsible for the synchronization failure. In this study, an analytic model taking account of the capsizing moment and stress singularity at the end of the contact interface is established to solve the contact pressure distribution. Then, a three-dimensional finite element model has been developed to analyze the transient thermal behavior of the conical friction element. The contact pressure and temperature distribution generated along the contact interfaces are investigated and compared between the proposed new model, the combined wear assumption, and the uniform pressure assumption. Furthermore, the variations in temperature obtained from the new model and the other two assumptions are compared to the experimental results. The results show that the temperature simulated by the new model has a good agreement with reality. The maximum temperatures obtained by the new model are 95.53 °C and 71.67 °C, and the measured values are respectively 84.98 °C and 65.46 °C at the measuring position under the given two working conditions.