This paper presents a syntactically-centered analysis of the loss of argumental dative case in the history of Greek. We treat the replacement strategies using accusative and genitive case as individual phenomena contributing to the same end, loss of dative. We argue that in Post-Classical times in possessor raising constructions the genitive possessor pronoun, given its clitic status, is attracted to the head of the Appl(icative)P(hrase) from within the possessee and comes to transfer its genitive Case feature to the head of ApplP. Once the applicative head has a genitive Case feature, it assigns inherent genitive Case to full noun phrases in the [Spec,ApplP]. The replacement of dative by accusative involves loss of the [dative] Case feature of v, resulting in the replacement of dative objects of monotransitive verbs by accusative ones in Medieval Greek. To account for the replacement of dative indirect objects by accusative indirect objects in the northern Greek dialects, we propose that accusative replaced genitive Case in Appl, but retained its inherent Case properties.