The complex geometry of historical buildings and the nonlinear behavior of masonry make the seismic assessment of these structures particularly challenging. This difficulty is further exacerbated when the buildings are subjected to seismic sequences. To address this issue, a novel methodology is proposed that combines pushover analysis on Finite Element (FE) models with the N2-method—a widely adopted approach in practice and recognized by both European and Italian building codes for evaluating seismic response. The innovation of the proposed procedure lies in its ability to assess structural capacity while accounting for cumulative damage induced by repeated seismic events. This strategy enables an efficient evaluation of damage progression. For each event in a given seismic sequence, the structural capacity curve is determined via nonlinear static analysis on the FE model. The N2-method is then employed to assess the resulting damage, which informs the modification of the FE model by adjusting the properties of the affected elements to reflect cumulative damage. In this way, seismic sequences are simulated through iterative nonlinear static analyses. The methodology is illustrated using a simple case study—a masonry arch with buttresses—and validated through a nonlinear time-history analysis.