Objectives: This study aimed to measure the level of medical-emergency-related knowledge among senior dental students and clinical trainers in Saudi Arabia. Methods: This cross-sectional pilot survey was conducted at Taibah Dental College, Madina, Saudi Arabia between March 2017 and November 2018. Two hundred and seventy-five self-administered anonymous questionnaires on the management of common medical emergencies were distributed to all senior dental students and clinical trainers at Taibah Dental College. Results: There was a serious lack of knowledge regarding the management of medical emergency scenarios among the participants. Only 54% of participants knew the correct management for some frequent and life-threating conditions such as “crushed chest pain”, and only 30–35% of participants knew the correct management of deeply sedated patients with benzodiazepine overdose and crisis of hypoadrenalism. Moderate-quality knowledge (50–74% of participants responded correctly) was noted for the following conditions: sudden onset of brain stroke, psychiatric patient, unconscious patient with hypoglycemia, patient with postural hypotension, and patient with hyperventilation. Based on the scale of knowledge, there were significant differences in the level of knowledge between clinical trainers, senior dental students, and junior dental students (p ≤ 0.01). Almost all students and 90% of trainers declared the need for further training. Conclusions: The overall knowledge regarding the management of medical emergency crises in the dental chair was moderate. However, the scale of knowledge regarding the management of medical emergency crises has gradually increased with the number of years of experience. Most participants recognize the need for further training.