Background: Prescription of medicines is the most prevalent treatment manner. Prescription writing errors may lead to a significant patient fatality. The aim of the current study was analyzing the quality of physicians’ prescriptions and prescribing trends in public and private health centers in Tripoli city of Libya. Methods: A cross-sectional study was conducted on 216 randomly selected prescriptions collected from a random sample of 35 community pharmacies over a study period of 72 working hours. Information about the drug categories and elements in the prescription was analyzed. Results: Our findings revealed that documentation was not ideally completed. Physician-related variables were mostly noted; however, the patient’s weight and diagnosis were missing in 10.1% and 26% of the prescriptions, respectively. Information regarding instruction to use the prescribed medications was missing in over 47% of the prescriptions. The average quantity of drugs per prescription was 3.0. Analgesics, antibiotics, and vitamin preparations were the most common classes of the prescribed drugs, respectively. Paracetamol, co-amoxiclav or amoxicillin, vitamin B complex, and pseudoephedrine were the specific medications, classified as highly frequent prescriptions. Conclusion: Trends of drug use in this study show that certain categories of drugs are overprescribed. The primary health-care physicians in Libya need ongoing training to progress their prescribing practices.