Earthquakes are natural disasters that can cause widespread devastation and loss of life. Simulated ground-motion records can be useful in regions with limited seismic stations or a history of damaging but infrequent earthquakes. This is especially true in areas with a high concentration of heritage masonry structures, which are especially susceptible to damage, as simulated records can be crucial in predicting their seismic response and protecting these buildings from seismic damage. Despite the importance of simulated earthquakes, few studies have investigated how effective they are compared to real earthquakes when assessing the structural response of heritage buildings. To address this knowledge gap, we employ two different simulation methods of the Mw 6.2 Faial earthquake, which occurred on July 9th, 1998, in the Azores, to replicate the recorded time-series at four available stations within an epicentral distance of 150 km. The study has two objectives: first, to validate the simulated records of the 1998 Faial earthquake using alternative stochastic ground-motion simulation approaches, and second, to determine how these approaches impact the seismic assessment of historic masonry structures. To accomplish these objectives, this study uses real and simulated ground-motion datasets to conduct non-linear response history analyses of the São Francisco Church, a monumental structure in Horta that sustained damage during the Faial earthquake. The results show that both simulation approaches yield structural responses similar to the observed records.