This dissertation investigates the patterning of Macedonian direct object DPs with respect to clitic pronouns. The occurrence of clitics with direct objects in Macedonian varies along two dimensions, the type of DP and the position of DP. Two broad classes are considered, regular and wh DPs, and positions both within IP and at the left periphery. The patterning of direct objects can be schematically represented as follows: [Special characters omitted.] The clitic co-occurrence restrictions in Macedonian are argued to be sensitive to the feature specification for strength of the DPs. Within each class of DPs, I show that there are well defined distinctions which correlate with the DPs' distinctive semantic properties. In particular, the specification of the regular DPs is linked to their strength in the sense of Barwise & Cooper (1981); the specification of the wh DPs is linked to their D-linking properties in the sense of Pesetsky (1987) and Comorovski (1996). The occurrence of the clitics is shown to be regulated by the Clitic Criterion (Sportiche 1998), with the clitic licensing a particular feature in the DP with which it co-occurs. The licensing is carried out through an agreement relation, in a Spec-Head configuration. It is proposed that only [+strong] DPs satisfy the Clitic Criterion. As such, within IP only strong DPs trigger the appearance of the clitic pronoun. At the left periphery, however, weak DPs can optionally occur with clitics. This can be explained through the possibility of some weak DPs entering into a binding relation with pro in argument position, which satisfies the Clitic Criterion. This explanation depends on a characterization of the DPs as [+strong], [-strong] and unspecified. I present arguments to establish that DPs at the left periphery that occur with clitics differ derivationally from those without clitics. I further establish on the basis of subject intervention effects, that wh-phrases with clitics occupy a higher position than wh-phrases without clitics, and suggest that the same holds for regular DPs. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]