One of the main research interests of the Tartu-Moscow Semiotic School was history. It started with Boris Uspensky and his paper Historia sub specie semioticae (1974), and was more comprehensively expanded in the last volume of the series Sign Systems Studies, entitled Semiotics and History (1992). The article focuses on two different approaches to semiotic and historical issues, which were expressed in the works of two leading representatives of the Tartu-Moscow Semiotic School, Yuri Lotman and Boris Uspensky. A comparative analysis of these different approaches enables us to reveal their starting points, assumptions and inspirations, as well as heuristic capabilities.