The Old City of Dubrovnik’s historical urban heritage architecture, consisting of poorly to well-built irregular stone masonry construction, is at high risk of earthquakes. It was enlisted as a UNESCO World Heritage after the severely damaging 1979 Mw = 7.1 Montenegro earthquake. Retrofitting strategies to a certain degree of earthquake protection have been made to the monument heritage architecture after repeating destructive earthquakes for several centuries. The originally 13th-century Rector’s Palace underwent several major modifications throughout history after disastrous events: fire in 1435, a gunpowder explosion in 1463, and earthquakes in 1520, 1667, and 1979. The design and construction information were collected from historical records and studies performed by various researchers, including field measurements and laboratory tests. Based on the data gathered, the building’s resistance to destructive earthquakes in compliance with contemporary building codes was determined using simulations on a calibrated spatial structural model. The study revealed that the building’s critical parts are most susceptible to a certain degree of damage or even collapse. The presented case study is the basis for decision-making and implementing the building’s earthquake risk reduction measures. Additionally, it will serve as a guide for earthquake risk evaluation on similar buildings, even though they may differ in degree or detail.