Methods and systems for syntactically indexing and searching data sets to achieve more accurate search results are provided. Example embodiments provide a Syntactic Query Engine ("SQE") that parses, indexes, and stores a data set, as well as processes natural language queries subsequently submitted against the data set. The SQE comprises a Query Preprocessor, a Data Set Preprocessor, a Query Builder, a Data Set Indexer, an Enhanced Natural Language Parser ("ENLP"), a data set repository, and, in some embodiments, a user interface. After preprocessing the data set, the SQE parses the data set and determines the syntactic and grammatical roles of each term to generate enhanced data representations for each object in the data set. The SQE indexes and stores these enhanced data representations in the data set repository. Upon subsequently receiving a query, the SQE parses the query similarly and searches the indexed stored data set to locate data that contains similar terms used in similar grammatical roles. In this manner, the SQE is able to achieve more contextually accurate search results more frequently than using traditional search engines.