Introduction:The evaluation of medical history questionnaire in dental clinics is essential to formulate a proper treatment plan in medically complex patients. Besides, it is also a source of information for future correspondence. The percentage of people suffering from chronic medical illness has been steadily increasing. Thus, it is imperative that the dentist will encounter patients with chronic illness in routine practice. Pre-administered questionnaires are the most commonly used and reliable method of evaluating medical health of the visiting patient. The intent of the question pertaining to medical health must be modulated based on the dental treatment requirement. This study intends to evaluate such a similar questionnaire and derive percentages of chronic illness afflicting patients visiting the dental college in a span of 3 months. Materials and Methods: A total of 725 patients were evaluated in the period of 3 months. The randomization of the sample was quantified by using a Tippets randomization table. A pre-tested questionnaire comprising of a list of medical ailments was used. A list of 16 ailments was included, and the answers were sought in monosyllables of yes or no. Besides, adverse habits were also evaluated as these are risk factors for the underlying systemic disease. The results were calculated by deriving simple percentage and then tabulated. Results: A total of 725 subjects were evaluated. Majority of the respondents were in the older age group. The most common chronic illness afflicting the respondents was hypertension, followed by Diabetes. Conclusion: Thorough evaluation of medical history is essential before beginning to start dental treatment. The analysis of the questionnaire in this study indicates toward the varied medical problems afflicting patients visiting the dental clinics. The dentist must be well conversant with the common diseases such as hypertension and diabetes in order to institute the correct treatment without affecting the general health of the patient.