Proper and precise embedding of commercial ads within Webpages requires Ad-hoc analysis and understanding of their content. By the successful implementation of this step, both publishers and advertisers gain mutual benefits through increasing their revenues on the one hand, and improving user experience on the other. In this research work, we propose a novel multi-level context-based ads serving approach through which ads will be served at generic publisher websites based on their contextual relevance. In the proposed approach, knowledge encoded in domain-specific and generic semantic repositories is exploited in order to analyze and segment Webpages into sets of contextually-relevant segments. Semantically-enhanced indexes are also constructed to index ads based on their textual descriptions provided by advertisers. A modified cosine similarity matching algorithm is employed to embed each ad from the Ads repository into one or more contextually-relevant segments. In order to validate our proposal, we have implemented a prototype of an ad serving system with two datasets that consist of (11429 ads and 93 documents) and (11000 documents and 15 ads), respectively. To demonstrate the effectiveness of the proposed techniques, we experimentally tested the proposed method and compared the produced results against five baseline metrics that can be used in the context of ad serving systems. In addition, we compared the results produced by our system with other state-of-the-art models. Findings demonstrate that the accuracy of conventional ad matching techniques has improved by exploiting the proposed semantically-enhanced context-based ad serving model.