In the upcoming period, city squares’ urban redesign will be crucial in achieving sustainable development goals. This study presents a systematic review of OTC-related studies for the urban design of city squares using the PRISMA 2020 methodology. A review included a total of 173 papers from 2001 to 2023. The results identified five study types—clusters based on four pre-defined criteria: study approach, data collection methods, time duration, and primary objectives. The clusters indicate that more than half of all studies are related to the comparison of thermal comfort and heat mitigation measures. Most of the case studies were located in one of three climate zones: temperate oceanic (Cfb) (58 studies), hot summer Mediterranean (Csa) (40 studies), or humid subtropical (Cfa) (28 studies). The most common geometry of the analyzed urban square is medium-sized, is rectangular, and has dominant axel orientation south–north. Also, based on all five clusters, several research gaps were identified, appropriate for future research: the majority of studies related to the traditionally considered climate areas, no typology of urban square geometry configuration based on OTC assessment, and the lack of a local design model for assessing and improving the thermal comfort of city squares.