Thirty-three samples of window glass and five glass lumps coming from three Italian archaeological sites—the Suasa excavations (Ancona, settled from the third century bc to the fifth to sixth centuries ad), the Roman town of Mevaniola (Forlì-Cesena, settled from the Imperial Age up to the fourth century ad) and Theodoric's Villa of Galeata (Forlì-Cesena, settled from the sixth century ad onwards)—were analysed to track the changes in the chemical composition and manufacturing technology of window glass through the centuries. The aims of this study were: (1) to establish the origin of the raw materials; (2) to verify the chemical homogeneity among samples coming from different sites and/or produced using different techniques; and (3) to sort the samples into the compositional groups of ancient glass. The analysis of all the chemical variables allowed two groups to be distinguished: (a) finds from Mevaniola and Suasa; and (b) finds from Galeata. All the samples had a silica–soda–lime composition, but the analysis of minor elements—in particular, of Fe, Mn, and Ti—made it possible to split the samples into two groups, with the higher levels of these elements always found in the Galeata samples (HIMT glass). In conclusion, it can be asserted that the main differences between the samples are related to their chronology.