In this analysis, I use a typological perspective to compare certain grammatical features of modern Southern Min dialects sch as Taiwanese and Amoy (Xiamen) with those found in the Southern Min translation of the Doctrina Christiana (ca. 1607 AD) and a Southern Min grammar written in Spanish: Arte de la lengua Chio Chiu (1620 AD). The specific grammatical constructions and categories which are investigated are dative, causative and passive constructions formed with kit(sic), 'to give;' comitative, ablative and benefactive constructions formed with cang (sic) (ka) 'with;' and the development of the diminutive marker -kia, -ia and -nia (sic) (-a) from the lexeme 'son.' The objective is to ascertain if these syntactic and morphological constructions have undergone any major grammatical changes over the last 4 centuries in Soutehrn Min. In fact, some functions of these markers prove to be similar to Taiwanese Soutehrn Min, such as certain uses of comitative cang (sic) (ka), while other markers appear to be distinct but are found elsewhere in Min dialects, such as the passive and causative marker kit (sic) (khit). The findings illustrate examples of grammatical renovation as the consequence of competing forms, phonological attrition and polysemous conceptual shift as the outcome of different paths of grammaticalization.