Semantic relatedness, or its inverse, semantic distance, measures the degree of closeness between two pieces of text determined by their meaning. Related work typically measures semantics based on a sparse knowledge base such as WordNet or Cyc that requires intensive manual efforts to build and maintain. Other work is based on a corpus such as the Brown corpus, or more recently, Wikipedia. This dissertation proposes two approaches to applying semantic relatedness to the problem of suggesting transfer course equivalencies. Two course descriptions are given as input to feed the proposed algorithms, which output a value that can be used to help determine if the courses are equivalent. The first proposed approach uses traditional knowledge sources such as WordNet and corpora for courses from multiple fields of study. The second approach uses Wikipedia, the openly-editable encyclopedia, and it focuses on courses from a technical field such as Computer Science. This work shows that it is promising to adapt semantic relatedness to the education field for matching equivalencies between transfer courses. A semantic relatedness measure using traditional knowledge sources such as WordNet performs relatively well on non-technical courses. However, due to the "knowledge acquisition bottleneck," such a resource is not ideal for technical courses, which use an extensive and growing set of technical terms. To address the problem, this work proposes a Wikipedia-based approach which is later shown to be more correlated to human judgment compared to previous work. [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.]