The push for urban development and the rapid increase in population have left many historic urban cores vulnerable and subject to deterioration. SDG-11 is often mentioned as the goal in UNDP regeneration, revitalization, and preservation projects regarding historic urban sites around the globe. The goal emphasizes 10 targets that are complex in nature and require closer inspection regarding their interconnectedness when being utilized in real-world scenarios. The current study explores the complexities of the decision-making process in planning urban regeneration projects concerning targets of SDG-11. The study uses a Multi-Criteria Evaluation (MCE) method to investigate how and to what significance the targeted criteria were used in planning for two UNDP urban regeneration project zones in Cyprus. These cases have a complex cultural and socio-political dynamic and pose high contextual significance for the region; therefore, many of these targets are critical in achieving more sustainable regeneration projects. The data collection was done by critically examining the projects’ documentation and conducting interviews with experts involved in the two projects. The data is controlled for internal consistency and anomalies. The study makes its case by comparing the different approaches implemented in these two projects and how effective they were in achieving SDG-11 targets.