Introduction: Potentially inappropriate prescriptions (PIPs) have been defined as the prescribing of medications where the risk of adverse outcomes outweighs the benefit to patients. Some medications pose a greater risk than others. Nonsteroidal anti-inflammatory drugs (NSAIDs), antiplatelets, and anticoagulants are among the top offenders for preventable drug-related ER visits, hospitalizations and deaths. Methods: Data were collected through a retrospective electronic/paper chart review for all patients prescribed a target medication in two family medicine clinics in Winnipeg, Manitoba from June 2012 to June 2013. Results: The presence of at least one PIP was identified in 198 of 567 patients (35%). The most common PIP was the use of an oral NSAID with one or more gastrointestinal bleed risk factor without adequate gastro-protection. Conclusion: With over one-third of patients using NSAIDs, antiplatelets, and anticoagulants potentially inappropriately, a greater focus on improving prescribing practices with these higher-risk medications is warranted.