Responding to the need to develop an open source translation system, this paper aimed to present a prototype context-driven English to Cebuano machine translation system. The system was developed using the PHP programming language for easy and platform-independent deployment and MySQL for database management. It was piloted to 30 selected students using a piloted-tested survey questionnaire and test cases to evaluate the capability of the online translation system, technical and linguistic aspects. Findings show that the translation system was rated “Good” by the respondents based on George and Mallery’s rules of thumb. This means that it can translate English texts into Cebuano in a context-driven manner despite the latter’s ambiguity. The study further recommends additional morphological works and the use of object-oriented programming for future studies and development.