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Background: Short-term medical trips (STMTs) from high-resource countries frequently provide care in low and middle-income countries. Little existing literature objectively tracks the long-term outcomes of these interventions on the receiving populations over time to assess potential benefits and to ensure no harm is being done. Objectives: The purpose of this study was to objectively analyze the outcomes of a biannual STMT to Santo Domingo, Dominican Republic on hypertension (HTN), diabetes mellitus type 2 (DM2), and cardiovascular disease (CVD) risk over a five-year period (2015–2019). Methods: Data from 1655 patients was extracted from the electronic medical record. In patients who received treatment and had more than one visit, a linear mixed model was used to analyze effects on systolic blood pressure (SBP) and hemoglobin A1C (HbA1C) values over time. In patients with high CVD risk based on a non-laboratory-based assessment, provider compliance with prescribing an aspirin and statin was calculated and tracked over time. Results: In patients with HTN who received treatment, average SBP was 148.83 mmHg (SD = 23.96) at initial visit and demonstrated no change over time (Estimate: 0.68 mmHg/year increase, p = 0.46). HbA1C data was insufficient for analysis. Treatment for patients with high CVD risk with an aspirin and statin improved from 41.46% in 2015 to 70.51% in 2019. Conclusion: SBP in patients with HTN treated by this STMT demonstrated no significant change over time. Possible contributing factors included patient education, access and adherence to medications, and documentation of data. Provider compliance with appropriate prescribing was high for patients with HTN and DM2 and improved over time for patients with high CVD risk, serving as an indirect measure for potential long-term benefits on these populations. All STMTs should objectively track outcomes of their interventions to assess risks and benefits to the communities being served.