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The collapse of abandoned room-and-pillar mines is often violent and unpredictable. Safety concerns often resulted in mine closures with no post-mining stability evaluations. As a result, large amounts of land resources over room-and-pillar mines are wasted. This paper attempts to establish an understanding of the long-term stability issues of goafs (abandoned mines). Considering progressive pillar failures and the effect of single pillar failure on surrounding pillars, this paper proposes a pillar peeling model to evaluate the long-term stability of coal mines and the associated criteria for evaluating the long-term stability of room-and-pillar mines. The validity of the peeling model was verified by numerical simulation, and field data from 500 pillar cases from China, South Africa, and India. It is found that the damage level of pillar peeling is affected by the peel angle and pillar height and is controlled by the pillar width–height ratio.