Previous numerical–analytical approaches have suggested that the main range divide prefers to migrate towards the high uplift flank in the asymmetric tectonic uplift pattern. However, natural examples recording these processes and further verifying the numerical simulations results, are still lacking. In this study, the landscape features, and the probable drainage evolution history of the Zhongtiao Shan, a roughly west-east trending, half-horst block on the southernmost tip of the Shanxi Graben System, were investigated through the geomorphic analyses (i.e., slope and steepness distributions, and the Gilbert and χ metrics). The topographic slope and steepness results indicate that the Zhongtiao Shan, controlled by the north Zhongtiao Shan normal fault, experiences asymmetric uplift and erosion patterns, with higher uplift and erosion on the north range. In addition, the Gilbert and χ metrics suggest that the western part of the main divide is currently stable, while the eastern divide is moving southward. According to the drainage divide stability criteria, we suggest that the uplift and erosion, on the fault side, balance each other well on the western part of the range, while on the eastern part, the uplift is outpaced by the erosion. In addition, a dynamic divide migration model in the asymmetric uplift condition is proposed, indicating that the interaction between uplift and erosion controls the migration and/or stability of the main divide. Deducing through this dynamic model, we suggested that the eastern segment of the north Zhongtiaoshan Fault must have experienced higher activities in the geological history, and the western fault may remain its activity along with the mountain relief generation. This gives a case that specific information on asymmetric neotectonic history and landscape evolution in an orogenic mountain can be uncovered by the proposed dynamic model.